KR20230155973A - Heterocyclic compound, organic light emitting device including the same and electronic apparatus including the organic light emitting device - Google Patents

Abstract

A heterocyclic compound represented by the following formula (1A), an organic light-emitting device including the same, and an electronic device including the organic light-emitting device are provided:
<Formula 1A>

For a description of Formula 1A, refer to what is described herein.

Description

Heterocyclic compound, organic light emitting device including the same and electronic apparatus including the organic light emitting device}

A heterocyclic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device are provided.

An organic light emitting device is a self-emitting device, has excellent viewing angle, response time, luminance, driving voltage, and response speed, and can be multicolored.

According to one example, an organic light emitting device may include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including a light emitting layer. A hole transport region may be provided between the anode and the light-emitting layer, and an electron transport region may be provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate excitons. Light is generated as this exciton changes from the excited state to the ground state.

The object is to provide a novel heterocyclic compound, an organic light-emitting device employing the same, and an electronic device including the organic light-emitting device.

According to one aspect, a heterocyclic compound represented by Formula 1A is provided:

<Formula 1A>

In Formula 1A,

k1 is one of the integers from 1 to 5,

n1 is one of the integers from 1 to 3,

n2 is one of the integers from 0 to 3,

R ₁ to R ₄ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q _{3 )} (Q 4 )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),

R ₅ to R ₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),

d1, d2, d3, d5, and d6 are independently one of the integers from 0 to 4,

d4 is one of the integers from 0 to 3,

d7 is one of the integers from 0 to 5,

Of formula 1A: The moiety represented by is a group represented by one of the following formulas 5-1 to 5-9,

In formulas 5-1 to 5-9,

R ₅ to R ₇ are each the same as described above,

d75, d75' and d75" are independently one of the integers from 0 to 5,

d54, d64 and d64' are independently one of the integers from 0 to 4,

d53 is one of the integers from 0 to 3,

d52 is one of the integers from 0 to 2,

The heterocyclic compound represented by Formula 1 contains at least one deuterium,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group. The substituent is,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group, substituted in any combination;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any combination thereof, substituted or unsubstituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or

any combination thereof;

ego,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; amidino group; hydrazine group; hydrazone group; Carboxylic acid group or salt thereof; Sulfonic acid group or salt thereof; Phosphoric acid group or salt thereof; C ₁ -C ₆₀ alkyl group _substituted or unsubstituted _with deuterium, C 1 -C 60 alkyl group, C ₆ -C ₆₀ aryl group, or any combination thereof; 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 substituted or unsubstituted with deuterium, C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group, or _any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

According to another aspect, a first electrode; second 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 one or more of the heterocyclic compounds.

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

By using the heterocyclic compound represented by Formula 1A, an organic light-emitting device with long lifespan characteristics and an electronic device including the same can be provided.

Figure 1 is a cross-sectional view schematically showing an organic light-emitting device 10 according to an embodiment.

The heterocyclic compound may be represented by the following formula 1A:

<Formula 1A>

In Formula 1A, k1 may be one of the integers from 1 to 5.

According to one embodiment, k1 may be one of the integers from 1 to 3.

In Formula 1A,

n1 may be one of the integers from 1 to 3.

According to one embodiment, n1 may be 1 or 2.

n2 may be one of the integers from 0 to 3.

According to one embodiment, n2 may be 0 or 1.

R ₁ to R ₄ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q _{3 )} (Q 4 )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ).

R ₅ to R ₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ).

According to one embodiment, R ₁ to R ₄ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino. group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group. , substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted Ringed C ₆ -C ₆₀ arylthio group, -N(Q ₁ )(Q ₂ ), -Si(Q _{3 )} (Q 4 )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ).

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group. The substituent is,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group, substituted in any combination;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any combination thereof, substituted or unsubstituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or

any combination thereof; It can be.

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; amidino group; hydrazine group; hydrazone group; Carboxylic acid group or salt thereof; Sulfonic acid group or salt thereof; Phosphoric acid group or salt thereof; C ₁ -C ₆₀ alkyl group _substituted or unsubstituted _with deuterium, C 1 -C 60 alkyl group, C ₆ -C ₆₀ aryl group, or any combination thereof; 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 substituted or unsubstituted with deuterium, C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group, or _any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; monovalent non-aromatic condensed polycyclic group; Or it may be a monovalent non-aromatic heterocondensed polycyclic group.

In Formula 1A, d1, d2, d3, d5 and d6 each represent the number of R ₁ , R ₂ , R ₃ , R ₅ and R ₆ and, independently of each other, are integers from 0 to 4 (for example, 0 , 1, 2, 3 or 4). When d1 is 2 or more, two or more R ₁ 's are the same as or different from each other, when d2 is 2 or more, two or more R ₂ 's are the same or different from each other, and when d3 is 2 or more, two or more R ₃ 's are the same or different from each other. , when d5 is 2 or more, two or more R ₅ may be the same or different from each other, and when d6 is 2 or more, two or more R ₆ may be the same or different from each other.

In Formula 1A, d4 represents the number of R ₄ and may be an integer from 0 to 3 (for example, 0, 1, 2, or 3). When d4 is 2 or more, 2 or more R ₄ may be the same or different from each other.

In Formula 1A, d7 represents the number of R ₇ and may be one of the integers from 0 to 5 (for example, 0, 1, 2, 3, 4, or 5). When d7 is 2 or more, two or more R _7s may be the same or different from each other.

According to one implementation, at least one of d2 and d1 may be an integer of 1 or more. For example, at least one of d2 and d1 may be 4.

According to one embodiment, R ₁ to R ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF ₅ , C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group. ;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group or C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group substituted with any combination thereof;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazole Diary group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary group, imidazopyridinyl group or imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, Fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group , isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopy Ridinyl group, imidazopyrimidinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, ada Mantanyl group (adamantanyl), norbornanyl group (norbornanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazole Diary group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group , quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group. , tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group or imidazopyrimidinyl group; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ );

Q ₁ to Q ₉ and Q ₃₁ to Q ₃₃ are independently of each other,

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

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group or naph til group; or

Substituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, or naphthyl group.

According to one embodiment, R ₁ to R ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF ₅ , C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group. ;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group or C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group substituted with any combination thereof; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ );

Q ₁ to Q ₉ and Q ₃₁ to Q ₃₃ are independently of each other,

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

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group or naph til group; or

Substituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, or naphthyl group.

According to another embodiment, R ₁ to R ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group; or

A group represented by any one of Formulas 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-355; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

Q ₁ to Q ₅ are each as described herein:

In the above formulas 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-355, * is a binding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and t-Bu is a t-butyl group.

According to another embodiment, R ₁ to R ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group; or

A group represented by any one of Formulas 9-1 to 9-61 and 9-201 to 9-240; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

Q ₁ to Q ₅ are each as described herein:

In Formulas 9-1 to 9-61 and 9-201 to 9-240, * is a bonding site with a neighboring atom.

The heterocyclic compound represented by Formula 1A may contain at least one deuterium.

According to one embodiment, the heterocyclic compound may include deuterium as a substituent or part of the substituent.

According to one embodiment, the heterocyclic compound represented by Formula 1A may satisfy at least one of the following Conditions 1 to 7:

<Condition 1>

At least one of d1 R _1s is deuterium

<Condition 2>

At least one of d2 R _2s is deuterium

<Condition 3>

At least one of n1*d3 R _3s is deuterium

<Condition 4>

At least one of n1*d4 R _4s is deuterium

<Condition 5>

At least one of d5 R _5s is deuterium

<Condition 6>

At least one of k1*n2*d6 R _6s is deuterium

<Condition 7>

At least one of k1*d7 R _7s is deuterium.

For example, the heterocyclic compound may satisfy at least one of Condition 1 and Condition 2.

According to one embodiment, at least two of conditions 1 to 7 may be satisfied.

According to one embodiment, at least three of conditions 1 to 7 may be satisfied.

According to one embodiment, at least four of conditions 1 to 7 may be satisfied.

According to one embodiment, at least five of conditions 1 to 7 may be satisfied.

According to one embodiment, at least six conditions among conditions 1 to 7 may be satisfied.

According to one embodiment, all of conditions 1 to 7 above may be satisfied.

According to one embodiment, the heterocyclic compound represented by Formula 1A may satisfy at least one of the following conditions 1' to 7':

<Condition 1'>

All d1 R _1s are deuterium, and d1 is 4.

<Condition 2'>

All d2 R _2s are deuterium, and d2 is 4.

<Condition 3'>

All n1*d3 R _3s are deuterium, and d3 is 4.

<Condition 4'>

All n1*d4 R _4s are deuterium, and d4 is 3.

<Condition 5'>

All d5 R _5s are deuterium,

k1 is 1 and d5 is 4; or k1 is 2 and d5 is 3

<Condition 6'>

k1*n2*d6 R _6s are all deuterium, and d6 is 4

<Condition 7'>

All k1*d7 R _7s are deuterium, and d7 is 5.

According to one embodiment, at least two of conditions 1' to 7' may be satisfied.

According to one embodiment, at least three of conditions 1' to 7' may be satisfied.

According to one embodiment, at least four of conditions 1' to 7' may be satisfied.

According to one embodiment, at least five conditions among conditions 1' to 7' may be satisfied.

According to one embodiment, at least six conditions among conditions 1' to 7' may be satisfied.

According to one embodiment, all of the above conditions 1' to 7' may be satisfied.

According to one embodiment, the deuterium substitution rate of the heterocyclic compound represented by Formula 1A may be greater than 0% and less than or equal to 100%.

According to one embodiment, the deuterium substitution rate of the heterocyclic compound represented by Formula 1A may be about 10% or more and 100% or less. For example, the substitution rate of deuterium is about 10% or more and 100% or less, about 10% or more and about 90% or less, about 15% or more and 100% or less, about 15% or more and about 90% or less, about 20% or more and 100% or less, It may be about 20% or more and about 90% or less, about 40% or more and about 100% or less, or about 40% or more and about 90% or less.

According to one embodiment, the deuterium substitution rate of the heterocyclic compound may be about 40% or more and 90% or less.

The “deuterium substitution rate” refers to the ratio of the number of substituents substituted with deuterium among the number of substituents that can be substituted on the core of the heterocyclic compound represented by Formula 1A. That is, it means the ratio of the number of R ₁ to R ₇ of deuterium among the total number of R ₁ to R ₇ in Formula 1 A.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 10% or more of this may be deuterium.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 20% or more of this may be deuterium.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 30% or more of this may be deuterium.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 40% or more of this may be deuterium.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 80% or more of this may be deuterium.

According to one embodiment, d1 R _{1 ,} d2 R ₂ , n1*d3 R ₃ , n1*d4 R _{4 ,} d5 R ₅ , k1*n2*d6 R ₆ and k1*d7 R ₇ About 90% or less of this may be deuterium.

According to one embodiment, in Formula 1A, The moiety represented by may be a group represented by one of the following formulas 2-1 to 2-4:

In Formulas 2-1 to 2-4,

For descriptions of R ₃ , R ₄ , d3 and d4, refer to each description in the specification,

* and *' are binding sites with neighboring atoms.

According to one embodiment, in Formula 1A, The moiety represented by may be a group represented by one of the following formulas 3-1 to 3-20:

In Formulas 3-1 to 3-20,

R ₁₁ to R ₁₄ each refer to the description of R ₁ in the specification,

R ₂₁ to R ₂₄ each refer to the description of R ₂ in the specification,

R ₃₁ to R ₃₈ each refer to the description of R ₃ in the specification,

R ₄₁ to R ₄₈ each refer to the description of R ₄ in the specification,

* is a bonding site with a neighboring atom.

According to one embodiment, in Formulas 3-1 to 3-4, R ₁₁ to R _14, R ₂₁ to R _24, R ₃₁ to R ₃₄ and At least one of R ₄₁ to R ₄₄ may be deuterium.

According to one embodiment, in Formulas 3-1 to 3-4, R ₁₁ to R _14, R ₂₁ to R _24, R ₃₁ to R ₃₄ and Part or all of R ₄₁ to R ₄₄ may be deuterium.

According to one embodiment, in Formulas 3-5 to 3-20, R ₁₁ to R _14, R ₂₁ to R _24, R ₃₁ to R ₃₈ and At least one of R ₄₁ to R ₄₈ may be deuterium.

According to one embodiment, in Formulas 3-5 to 3-20, R ₁₁ to R _14, R ₂₁ to R _24, R ₃₁ to R ₃₈ and Part or all of R ₄₁ to R ₄₈ may be deuterium.

According to one embodiment, in Formula 1A, The moiety represented by may be a group represented by one of the following formulas 5-1 to 5-9.

In formulas 5-1 to 5-9,

R ₅ to R ₇ are each as described herein,

d75, d75' and d75" are independently one of the integers from 0 to 5,

d54, d64 and d64' are independently one of the integers from 0 to 4,

d53 is one of the integers from 0 to 3,

d52 may be one of the integers from 0 to 2.

According to one embodiment, the heterocyclic compound represented by Formula 1A may be represented by one of the following Formulas 1A-1 to 1A-12:

In formulas 1A-1 to 1A-12,

R ₁ to R ₅ each refer to the description in the specification,

d75, d75' and d75" may independently be one of the integers from 0 to 5,

d14, d24, d34, d34', d54, d64 and d64' may independently be one of the integers from 0 to 4,

d43, d43' and d53 may independently be one of the integers from 0 to 3,

d52 may be one of the integers from 0 to 2,

The heterocyclic compounds represented by Formulas 1A-1 to 1A-12 each contain at least one deuterium.

According to another embodiment, the heterocyclic compound represented by Formula 1A may be represented by one of the following Formulas 1-1 to 1-106:

In formulas 1-1 to 1-106,

At least one hydrogen may be replaced with deuterium.

According to one embodiment, in Formulas _1-1 to 1-106, all hydrogens except hydrogen substituted with _deuterium may be substituted with a _substituent R See explanation.

According to another embodiment, the heterocyclic compound represented by Formula 1A may be one of the following compounds 1 to 248:

The heterocyclic compound represented by Formula 1A has a first benzene group, a second benzene group, a first carbazole group, and a second carbazole group bonded in that order through a single bond, and in addition, a benzene group and a carbazole group. Each may be further included, and the "N" of the first carbazole group is bonded to the benzene group, and the "N" of the second carbazole group is bonded to the first carbazole group (Formula 1 below ' reference). As a result, it is possible to have a relatively high T ₁ energy level.

Additionally, the heterocyclic compound represented by Formula 1A contains at least one deuterium. Compared to the C-H bond, the C-D bond distance is close, the bond energy is high, the frequency is high, and the range of structural fluctuations is small, so the heterocyclic compound can have structural stability. Additionally, structures related to hole movement can have hole stability due to the kinetic isoptope effect.

<Formula 1'>

According to one embodiment, the heterocyclic compound represented by Formula 1A may have a triplet energy level of 2.8 eV or more, or in the range of 2.8 eV to 3.5 eV (for example, see Table 1 below).

According to another embodiment, the absolute HOMO energy level of the heterocyclic compound represented by Formula 1A may be 5.2 eV or less, 4.8 eV to 5.2 eV, or 5.0 eV to 5.2 eV (e.g., see Table 1 below) ).

The triplet energy level and HOMO energy level may be evaluated by DFT (density functional theory).

For example, the HOMO energy level, LUMO energy level, singlet (S1) energy level, and triplet (T ₁ ) energy level of compounds 22 and 98 belonging to the heterocyclic compound represented by Formula 1A above are expressed as B3LYP/6-31G ( The results of evaluation using structure-optimized DFT (e.g., DFT method of Gaussian program) at d,p) level are shown in Table 1 below:

Compound No. HOMO
(eV) LUMO
(eV) S ₁
(eV) T ₁
(eV) 10 -5.127 -1.144 3.605 3.149 54 -5.100 -0.960 3.820 3.318

The method for synthesizing the heterocyclic compound represented by Formula 1A can be recognized by those skilled in the art by referring to the synthesis examples described later.

According to another aspect, a first electrode; second 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 one or more heterocyclic compounds represented by Formula 1A.

The organic light emitting device may have high lifespan characteristics by providing an organic layer containing the heterocyclic compound represented by Chemical Formula 1A as described above.

The first electrode is an anode, which is a hole injection electrode, and the second electrode is a cathode, which is an electron injection electrode, or the first electrode is a cathode, which is an electron injection electrode, and the second electrode is an anode, which is a hole injection electrode.

For example, in the organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer includes a hole transport region disposed between the first electrode and the light-emitting layer and the light-emitting layer and the second electrode. It further includes an electron transport region disposed therebetween, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, an auxiliary layer, or any combination thereof, and the electron transport region includes a buffer layer and a hole blocking layer. layer, an electron transport layer, an electron injection layer, or any combination thereof.

The heterocyclic compound represented by Formula 1A can be used between a pair of electrodes of an organic light-emitting device. For example, the heterocyclic compound represented by Formula 1A may be included in the light-emitting layer. At this time, the heterocyclic compound serves as a host, and the light-emitting layer may further include a dopant (that is, the content of the heterocyclic compound represented by Formula 1A is greater than the content of the dopant). For example, the light emitting layer may emit blue light.

According to one embodiment, the heterocyclic compound may be included in the hole transport region. For example, the heterocyclic compound may be included in the auxiliary layer of the hole transport region.

According to one embodiment, the heterocyclic compound may be included in the electron transport region. For example, the heterocyclic compound may be included in the buffer layer of the electron transport region.

According to one embodiment, the light-emitting layer includes a host and a dopant, and the host may include the heterocyclic compound. For example, the content (weight) of the host may be greater than the content (weight) of the dopant.

According to another embodiment, blue light may be emitted from the light emitting layer, but the present invention is not limited thereto.

The dopant may be a fluorescent dopant, a phosphorescent dopant, or any combination thereof. For example, the dopant may be a phosphorescent dopant.

According to one embodiment, the light-emitting layer includes a host, a fluorescent dopant, and a phosphorescent dopant, and the host may include the heterocyclic compound. At this time, the phosphorescent dopant may be a sensorizer compound that is used together with a fluorescent dopant to transfer excitons to the fluorescent dopant.

As used herein, “(the organic layer) includes one or more heterocyclic compounds” means “(the organic layer) includes one type of heterocyclic compound belonging to the category of Formula 1A above or two different types of heterocyclic compounds belonging to the category of Formula 1A above. It can be interpreted as “may include more than one heterocyclic compound.”

For example, the organic layer may include only Compound 1 as the heterocyclic compound. At this time, 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 heterocyclic compound. At this time, Compound 1 and Compound 2 may exist in the same layer (for example, Compound 1 and Compound 2 may both exist in the emission layer).

As used herein, “organic layer” is a term referring to a single and/or multiple layers disposed between a first electrode and a second electrode in an organic light emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes containing metals.

Description of Figure 1

Figure 1 schematically shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. Hereinafter, the structure and manufacturing method of an organic light-emitting device according to an embodiment of the present invention will be described with reference to FIG. 1.

The organic light emitting device 10 of FIG. 1 includes a first electrode 11, a second electrode 19 opposite the first electrode 11, and a space between the first electrode 11 and the second electrode 19. It includes an organic layer (10A) disposed on.

The organic layer 10A includes a light-emitting layer 15, a hole transport region 12 is disposed between the first electrode 11 and the light-emitting layer 15, and the light-emitting layer 15 and the second electrode An electron transport region (17) is disposed between (19).

A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a typical organic light emitting device can be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance can be used.

[First electrode (11)]

The first electrode 11 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. The first electrode 11 may be an anode. The material for the first electrode may include a material with a high work function to facilitate hole injection.

The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 11, 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), or a material thereof. Any combination may be included. Alternatively, to form the first electrode 110, which is a transflective electrode or a reflective electrode, the first electrode material is magnesium (Mg), silver (Ag), aluminum (Al), or aluminum-lithium (Al-Li). ), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

The first electrode 11 may have a single layer or a multi-layer structure including two or more layers.

[Luminous layer (15)]

The thickness of the light emitting layer 15 may be about 100Å to about 1000Å, for example, about 200Å to about 600Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[Host in the light-emitting layer (15)]

The host in the light emitting layer 15 may include a heterocyclic compound represented by Formula 1A.

In addition to the heterocyclic compound represented by Formula 1A (for example, see the first host in the examples below), it may further include an arbitrary host (for example, see the second host in the examples below). Hereinafter, hosts that may be included in the light-emitting layer 15 in addition to the heterocyclic compound represented by Formula 1A will be described.

The host may contain no transition metal.

The host may be one type of compound or a mixture of two or more different compounds.

According to one embodiment, the host may include at least one of an amphipathic host, an electron-transporting host, and a hole-transporting host. The amphiphilic host, electron-transporting host, and hole-transporting host may each be different from each other.

The electron transporting host may include at least one electron transporting group.

The hole transporting host may not include an electron transporting group.

As used herein, an “electron transporting group” may include a cyano group, an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, a group represented by one of the following formulas, or any combination thereof:

In the above formula, *, *', and *" are each a binding site with an arbitrary neighboring atom.

According to one embodiment, the electron-transporting host may include at least one of a cyano group and an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group.

According to another embodiment, the electron transporting host may include at least one cyano group.

According to another embodiment, the electron-transporting host may include at least one cyano group and an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group.

According to another embodiment, the host may include an amphipathic host.

According to another embodiment, the host may include an electron transporting host.

According to another embodiment, the host may include a hole transporting host.

According to another embodiment, the hole transporting host is mCP (1,3-bis(9-carbazolyl)benzene), TCTA (Tris(4-carbazoyl-9-ylphenyl)amine), CBP(4,4'-Bis (N-carbazolyl)-1,1'biphenyl), mCBP(3,3-bis(carbazol-9-yl)bipheny), NPB(N,N'-di(1-naphthyl)-N,N'-diphenyl -(1,1'-biphenyl)-4,4'diamine), m-MTDATA(4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine) and TPD(N,N'-bis It may not be (3-methylphenyl)-N,N'-diphenylbenzidine).

According to another implementation,

The host includes an electron-transporting host and a hole-transporting host,

The electron-transporting host comprises at least one ð electron-rich C ₃ -C ₆₀ cyclic group and at least one electron-transporting group,

wherein the hole transporting host comprises at least one ð electron-excessive C ₃ -C ₆₀ cyclic group and does not contain an electron transporting group;

The electron transporting group may include a cyano group, an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, or any combination thereof.

According to another embodiment, the electron transporting host may include i) at least one of a cyano group, a pyrimidine group, a pyrazine group, and a triazine group, and ii) at least one of a triphenylene group and a carbazole group.

According to another embodiment, the hole transporting host may include at least one carbazole group.

According to another embodiment, the electron transporting host includes a compound represented by the following formula E-1,

The hole transporting host may include a compound represented by the following formula H-1:

<Formula E-1>

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

In Formula E-1,

Ar ₃₀₁ is a C ₅ -C ₆₀ carbocyclic group unsubstituted or substituted with at least one R _301a or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _301a ,

xb11 is 1, 2 or 3,

L ₃₀₁ are each independently a single bond, a group represented by one of the following formulas, a C ₅ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _301a , or C substituted or unsubstituted with at least one R _{301a 1} -C ₆₀ It is a heterocyclic group, and in the formula below, *, *' and *" are each a bonding site with an arbitrary neighboring atom,

xb1 is an integer from 1 to 5,

R _301a and R ₃₀₁ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ), -N(Q ₃₀₁ )(Q ₃₀₂ ), -B(Q ₃₀₁ )(Q ₃₀₂ ), -C (=O)(Q ₃₀₁ ), -S(=O) ₂ (Q ₃₀₁ ), -S(=O)(Q ₃₀₁ ), -P(=O)(Q ₃₀₁ )(Q ₃₀₂ ) or -P( =S)(Q ₃₀₁ )(Q ₃₀₂ ),

xb21 is an integer from 1 to 5,

Q ₃₀₁ to Q ₃₀₃ 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,

At least one of the following <Condition 1"> to <Condition 3"> is satisfied:

<Condition 1">

At least one of Ar ₃₀₁ , L ₃₀₁ and R ₃₀₁ of the formula E-1 independently of one another includes an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group.

<Condition 2">

L ₃₀₁ in Formula E-1 is a group represented by one of the following formulas:

<Condition 3">

R ₃₀₁ in the formula E-1 is a cyano group, -S(=O) ₂ (Q ₃₀₁ ), -S(=O)(Q ₃₀₁ ), -P(=O)(Q ₃₀₁ )(Q ₃₀₂ ) or -P(=S)(Q ₃₀₁ )(Q ₃₀₂ )

<Formula H-1>

Ar ₄₀₁ -(L ₄₀₁ ) _xc1 -(Ar ₄₀₂ ) _xc11

Among the formulas H-1, 11 and 12,

L ₄₀₁ is

single bond; or

Deuterium, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, triphenylenyl group, biphenyl group, terphenyl group , tetraphenyl group, -Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), or any combination thereof, substituted or unsubstituted ð electron-excessive C ₃ -C ₆₀ cyclic group;

ego,

xc1 is an integer from 1 to 10, and when xc1 is 2 or more, 2 or more L ₄₀₁ are the same or different from each other,

Ar ₄₀₁ is a group represented by Formula 11 or 12 above,

Ar ₄₀₂ is,

A group represented by Formula 11 or 12; or

Deuterium, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, triphenylenyl group, biphenyl group, terphenyl group , tetraphenyl group, or substituted or unsubstituted in any combination, ð electron-excessive C ₃ -C ₆₀ cyclic group (e.g., phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, di benzothiophenyl group, biphenyl group, terphenyl group or triphenylenyl group);

ego,

xc11 is an integer from 1 to 10, and when xc11 is 2 or more, 2 or more Ar ₄₀₂ are the same or different from each other,

CY ₄₀₁ and CY ₄₀₂ are independently of each other, ð electron-excessive C ₃ -C ₆₀ cyclic group (benzene group, naphthalene group, fluorene group, carbazole group, benzocarbazole group, indolocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, benzonaphthofuran group, benzonaphthothiophene group or benzonaphthosilol group),

A ₂₁ is a single bond, O, S, N(R ₄₁₁ ), C(R ₄₁₁ )(R ₄₁₂ ) or Si(R ₄₁₁ )(R ₄₁₂ ),

A ₂₂ is a single bond, O, S, N(R ₄₁₁ ), C(R ₄₁₁ )(R ₄₁₂ ) or Si(R ₄₁₁ )(R ₄₁₂ ),

At least one of A ₂₁ and A ₂₂ in Formula 12 is not a single bond,

R ₄₀₁ , R ₄₀₂ , R ₄₁₁ and R ₄₁₂ are independently of each other,

Hydrogen, deuterium, C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group;

C ₁ -C 20 alkyl group or C ₁ -C ₂₀ alkoxy group substituted with deuterium, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, _{dibenzothiophenyl} group, or any combination thereof;

Substituted with deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, or any combination thereof or unsubstituted, ð electron-excessive C ₃ -C ₆₀ cyclic group; or

-Si(Q ₄₀₄ )(Q ₄₀₅ )(Q ₄₀₆ );

ego,

e1 and e2 are independently from each other, 0 to 10,

Q ₄₀₁ to Q ₄₀₆ are each independently selected from hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group Or a triphenylenyl group,

* is a bonding site with a neighboring atom.

According to one embodiment, in Formula E-1, Ar ₃₀₁ and L ₃₀₁ are each independently selected from deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, and nitro group. , amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group. , terphenyl group, naphthyl group, cyano-containing phenyl group, cyano-containing biphenyl group, cyano-containing terphenyl group, cyano-containing naphthyl group, pyridinyl group, phenylpyridinyl group, diphenylpyridinyl group, non. Phenylpyridinyl group, di(biphenyl)pyridinyl group, pyrazinyl group, phenylpyrazinyl group, diphenylpyrazinyl group, biphenylpyrazinyl group, di(biphenyl)pyrazinyl group, pyridazinyl group, phenyl Pyridazinyl group, diphenylpyridazinyl group, biphenylpyridazinyl group, di(biphenyl)pyridazinyl group, pyrimidinyl group, phenylpyrimidinyl group, diphenylpyrimidinyl group, biphenylpyrimidinyl group, Di(biphenyl)pyrimidinyl group, triazinyl group, phenyltriazinyl group, diphenyltriazinyl group, biphenyltriazinyl group, di(biphenyl)triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )( Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), - P(=O)(Q ₃₁ )(Q ₃₂ ), or any combination thereof, substituted or unsubstituted, benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, di Benzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, inde Noanthracene group, dibenzofuran group, dibenzothiophene group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, Pyrimidine 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, isobenzothiazole group, benzoxazole group, isobenzooxazole group, triazole group, tetrazole group, oxadiazole group, A triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group,

At least _{one of} Hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, cyano- containing phenyl group, cyano-containing biphenyl group, cyano-containing terphenyl group, cyano-containing naphthyl group, pyridinyl group, phenylpyridinyl group, diphenylpyridinyl group, biphenylpyridinyl group, di (biphenyl) Pyridinyl group, pyrazinyl group, phenylpyrazinyl group, diphenylpyrazinyl group, biphenylpyrazinyl group, di(biphenyl)pyrazinyl group, pyridazinyl group, phenylpyridazinyl group, diphenylpyridazinyl group, biphenylpyridazinyl group, di(biphenyl)pyridazinyl group, pyrimidinyl group, phenylpyrimidinyl group, diphenylpyrimidinyl group, biphenylpyrimidinyl group, di(biphenyl)pyrimidinyl group, tria Zinyl group, phenyltriazinyl group, diphenyltriazinyl group, biphenyltriazinyl group, di(biphenyl)triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ ) (Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)(Q ₃₁ )( Q ₃₂ ), or substituted or unsubstituted with any combination thereof, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group , pyrimidine 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, isobenzothiazole group, benzoxazole group, isobenzooxazole group, triazole group, tetrazole group, oxadiazole group , a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group,

R ₃₀₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its Salt, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, tetraphenyl group, naphthyl group, cyano-containing phenyl group, cyano -containing biphenyl group, cyano-containing terphenyl group, cyano-containing tetraphenyl group, cyano-containing naphthyl group, pyridinyl group, phenylpyridinyl group, diphenylpyridinyl group, biphenylpyridinyl group, di(bi Phenyl) pyridinyl group, pyrazinyl group, phenylpyrazinyl group, diphenylpyrazinyl group, biphenylpyrazinyl group, di(biphenyl)pyrazinyl group, pyridazinyl group, phenylpyridazinyl group, diphenylpyrazinyl group dazinyl group, biphenylpyridazinyl group, di(biphenyl)pyridazinyl group, pyrimidinyl group, phenylpyrimidinyl group, diphenylpyrimidinyl group, biphenylpyrimidinyl group, di(biphenyl)pyrimidinyl group , triazinyl group, phenyltriazinyl group, diphenyltriazinyl group, biphenyltriazinyl group, di(biphenyl)triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) or -P(=O)(Q ₃₁ )(Q ₃₂ ),

Q ₃₁ to Q ₃₃ may each independently be 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.

According to different implementations,

The Ar ₃₀₁ is deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or thereof. Salt, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, cyano-containing phenyl group, cyano-containing ratio. Phenyl group, cyano-containing terphenyl group, cyano-containing naphthyl group, pyridinyl group, phenylpyridinyl group, diphenylpyridinyl group, biphenylpyridinyl group, di(biphenyl)pyridinyl group, pyrazinyl group, Phenylpyrazinyl group, diphenylpyrazinyl group, biphenylpyrazinyl group, di(biphenyl)pyrazinyl group, pyridazinyl group, phenylpyridazinyl group, diphenylpyridazinyl group, biphenylpyridazinyl group , di(biphenyl)pyridazinyl group, pyrimidinyl group, phenylpyrimidinyl group, diphenylpyrimidinyl group, biphenylpyrimidinyl group, di(biphenyl)pyrimidinyl group, triazinyl group, phenyltriazinyl group, Diphenyltriazinyl group, biphenyltriazinyl group, di(biphenyl)triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B( Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), -P(=O)(Q ₃₁ )(Q ₃₂ ), or any of them. Substituted or unsubstituted in combination, benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluorane ten group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, or dibenzothiophene group; or

A group represented by one of the following formulas 5-1 to 5-3 and formulas 6-1 to 6-33;

ego,

The L ₃₀₁ may be a group represented by one of the following formulas 5-1 to 5-3 and 6-1 to 6-33:

In formulas 5-1 to 5-3 and 6-1 to 6-33,

Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or these Salt, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, cyano-containing phenyl group, cyano-containing ratio. Phenyl group, cyano-containing terphenyl group, cyano-containing naphthyl group, pyridinyl group, phenylpyridinyl group, diphenylpyridinyl group, biphenylpyridinyl group, di(biphenyl)pyridinyl group, pyrazinyl group, Phenylpyrazinyl group, diphenylpyrazinyl group, biphenylpyrazinyl group, di(biphenyl)pyrazinyl group, pyridazinyl group, phenylpyridazinyl group, diphenylpyridazinyl group, biphenylpyridazinyl group , di(biphenyl)pyridazinyl group, pyrimidinyl group, phenylpyrimidinyl group, diphenylpyrimidinyl group, biphenylpyrimidinyl group, di(biphenyl)pyrimidinyl group, triazinyl group, phenyltriazinyl group, Diphenyltriazinyl group, biphenyltriazinyl group, di(biphenyl)triazinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B( Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) or -P(=O)(Q ₃₁ )(Q ₃₂ ),

d4 is 0, 1, 2, 3 or 4,

d3 is 0, 1, 2 or 3,

d2 is 0, 1 or 2,

* and *' are each binding sites with neighboring atoms.

For a description of Q ₃₁ to Q ₃₃ , refer to what is described in the present specification.

According to another embodiment, L ₃₀₁ may be a group represented by one of Formulas 5-2, 5-3, and 6-8 to 6-33.

According to another embodiment, R ₃₀₁ is a cyano group or a group represented by one of the following formulas 7-1 to 7-18, and at least one of xc11 Ar ₄₀₂ is a group represented by one of the following formulas 7-1 to 7-18 It can be:

In formulas 7-1 to 7-18,

xb41 to xb44 are 0, 1 or 2, but xb41 in formulas 7-10 is not 0, xb41 + xb42 in formulas 7-11 to 7-13 is not 0, and xb41 + in formulas 7-14 to 7-16 xb42 + xb43 is not 0, xb41 + xb42 + xb43 + xb44 in Chemical Formulas 7-17 and 7-18 is not 0, and * is a bonding site with a neighboring atom.

In the formula E-1, two or more Ar ₃₀₁ are the same as or different from each other, two or more L ₃₀₁ are the same as or different from each other, two or more L ₄₀₁ in the formula H-1 are the same or different from each other, and two or more Ar ₄₀₂ are the same as each other. are the same or different from each other.

According to one embodiment, the electron transporting host may be represented by the following formula E-2:

<Formula E-2>

According to one embodiment, in Formula E-2, CY ₂₃ and CY ₂₄ may independently be a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

For example, CY ₂₃ and CY ₂₄ are independently of each other, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3 , 4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, thiophene group, furan group, indole group, benzoborole group, benzophosphopol group, indene group, benzosilol group, benzogermol group, benzo Thiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzo Selenophen group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzo Phosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzo Phosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group , aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, Quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group , thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline It may be a (5,6,7,8-tetrahydroisoquinoline) group or a 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group.

According to one embodiment, CY ₂₃ and CY ₂₄ may independently be a benzene group, a naphthalene group, or a pyridine group.

According to one embodiment, in Formula E-2, X ₂₁ may be N or C(R _21a ), X ₂₂ may be N or C(R _22a ), and X ₂₃ may be N or C(R _23a ). .

According to one embodiment, at least one of X ₂₁ to X ₂₃ in Formula E-2 may be N.

For example, one of X ₂₁ to X ₂₃ may be N, two of X ₂₁ to X ₂₃ may be N, and each of X ₂₁ to X ₂₃ may be N.

According to one embodiment, in Formula E-2, L ₂₁ and L ₂₂ are each independently a single bond, a substituted or unsubstituted C ₃ -C ₆₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C There may be ₆₀ heterocyclic groups.

For example, L ₂₁ and L ₂₂ are independently a single bond; or

Substituted or unsubstituted with at least one R _10a , benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4 -Tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophen group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophen group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza -9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thia Diazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5 ,6,7,8-tetrahydroisoquinoline) group or 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group; The description of R _10a is the same as the description of R ₂₃ in this specification.

According to one embodiment, in Formula E-2, L ₂₁ and L ₂₂ are each independently a single bond; Or it may be a group represented by any of the following formulas L-1 to L-12:

In the formulas L-1 to L-12,

Z ₂₁ and Z ₂₂ are each the same as the description for R ₂₁ in the specification,

d21 and d22 may be independently integers from 0 to 4,

d23 may be an integer from 0 to 3,

* and *' are each binding sites with neighboring atoms.

According to one embodiment, n21 to n22 in Formula E-2 each represent the number of L ₂₁ and L ₂₂ and, independently of each other, are integers from 0 to 5 (for example, 0, 1, 2, or 3). ) can be. When n21 is 2 or more, two or more L ₂₁ 's may be the same or different from each other, and when n22 is 2 or more, two or more L ₂₂ 's may be the same or different from each other.

According to one embodiment, in Formula E-2, R ₂₁ to R ₂₄ , R _21a , R _22a and R _23a are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group. , cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or an unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, or a 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 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, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent Non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), - It may be B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ ).

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ) , -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ ) (Q ₁₉ ) or a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group substituted with any combination thereof;

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, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthi group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge( C ₃ - substituted with Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ) or any combination thereof. C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) or -P(=O)(Q ₃₈ )(Q ₃₉ );

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted Substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ - C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group; Or it may be a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

In Formula E-2, b21 to b24 each represent the number of R ₂₁ to R ₂₄ and may independently be an integer from 0 to 10 (for example, 0, 1, 2, or 3). When b21 is 2 or more, 2 or more R ₂₁ 's are the same as or different from each other, when b22 is 2 or more, 2 or more R ₂₂ 's are the same or different from each other, and when b23 is 2 or more, 2 or more R ₂₃ 's are the same or different from each other. , when b24 is 2 or more, 2 or more R ₂₄ may be the same or different from each other.

For example, in Formula E-2, R ₂₁ to R ₂₄ , R _21a , R _22a and R _23a are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, -SF ₅ , C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group. ;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group or C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group substituted with any combination thereof;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazole Diary group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary group, imidazopyridinyl group or imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, Fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group , isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopy Ridinyl group, imidazopyrimidinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, ada Mantanyl group (adamantanyl), norbornanyl group (norbornanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazole Diary group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group , quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group. , tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group or imidazopyrimidinyl group; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ );

Q ₁ to Q ₉ and Q ₃₁ to Q ₃₃ are independently of each other,

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

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group or naph til group; or

Substituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, or naphthyl group.

According to one embodiment, R ₂₁ to R ₂₄ , R _21a , R _22a and R _23a are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ -C ₆₀ alkoxy group; or

A group represented by any one of Formulas 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-355; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

Q ₁ to Q ₅ are each as described herein:

In the above formulas 9-1 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-355, * is a binding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, TMG is a trimethylgermyl group, and t-Bu is a t-butyl group.

According to one embodiment, R ₂₁ and R ₂₂ are each independently substituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), or any combination thereof. substituted or unsubstituted, phenyl group, naphthyl group or carbazolyl group; or -Si(Q ₃ )(Q ₄ )(Q ₅ );

Q ₁ to Q ₃ are each independently a phenyl group or naphthyl group substituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) or any combination thereof; ,

Q ₃₃ to Q ₃₅ may each independently be a phenyl group or a naphthyl group substituted with deuterium, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof.

According to one embodiment, R ₂₁ and R ₂₂ are independently of each other, a C ₆ -C ₆₀ aryl group substituted or unsubstituted with at least one R _10a , a group represented by Formula E-2A below, or Formula E-2B below. It can be a marked group,

The R _10a is the same as the description for R ₂₃ in Formula E-2 in the specification:

<Formula E-2A>

<Formula E-2B>

Among the formulas E-2A and E-2B,

The description of Z ₂₃ to Z ₂₇ is the same as the description of R ₂₃ in this specification,

d24 and d25 may be independently integers from 1 to 4,

d26 to d30 may be independently integers from 1 to 5,

L ₂₃ is the same as the description for L ₂₁ in this specification,

n23 may be an integer from 1 to 5,

m23 may be an integer from 0 to 3,

* is a bonding site with a neighboring atom.

Specific examples of the electron transporting host may refer, for example, to compounds of the following groups HE1 to HE8:

<Group HE1>

<Group HE2>

<Group HE3>

<Group HE4>

<Group HE5>

<Group HE6>

<Group HE7>

<Group HE8>

As another example, the hole transporting host may include at least one of the following compounds H-H1 to H-H103:

As another example, the amphiphilic host may refer to the compounds of group HEH1:

<Group HEH1>

In this specification, Ph is a phenyl group.

According to one embodiment, the following compound H1 can be used as the hole transporting host. According to another embodiment, as the electron transporting host, the following compound H2 may be used:

[Dopant in light-emitting layer (15)]

The dopant in the light emitting layer 15 may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

According to one embodiment, the light-emitting layer 15 includes a host, a fluorescent dopant, and a phosphorescent dopant, and the host may include the heterocyclic compound. At this time, the phosphorescent dopant may be a sensorizer compound that is used together with a fluorescent dopant to transfer excitons to the fluorescent dopant.

For example, the phosphorescent dopant may be a blue dopant.

Phosphorescent dopant

According to one embodiment, the phosphorescent dopant may include a transition metal and a tetradentate ligand. According to another embodiment, the phosphorescent dopant may include a transition metal and one or more monodentate ligands, bidentate ligands, and tridentate ligands.

According to one embodiment, the phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 31:

<Formula 31>

In Formula 31, M ₃₁ is a transition metal.

According to one embodiment, M ₃₁ may be Pt, Pd, or Au.

In Formula 31, X ₃₁ to X ₃₄ are each independently C or N,

Among the bonds between X ₃₁ and M ₃₁ , _{the bond} between X ₃₂ and M ₃₁ , the bond between X ₃₃ and M ₃₁ , and the bond between .

According to one embodiment, the bond between X ₃₁ and M ₃₁ may be a coordination bond.

According to one embodiment, X ₃₁ is C, and the bond between X ₃₁ and M ₃₁ may be a coordination bond. That is, in Formula 31, X ₃₁ may be C in the carbene moiety.

In Formula 31, CY ₃₁ to CY ₃₄ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, CY ₃₁ to CY ₃₄ are independently of each other,

i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) one or more first rings and one or more The second ring is a condensed ring condensed with each other,

The first ring is a cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silole group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, Isoxatriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thitriazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, tetra A sol group, an azacylol group, a diazacylol group, or a triazacylol group,

The second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, and a pyridazine group. , a triazine group, an oxazine group, a thiazine group, a dihydropyrazine group, a dihydropyridine group, or a dihydroazasilane group.

적어도 하나의 R_10a로 치환 또는 비치환된 C₅-C₃₀카보시클릭 그룹 또는 적어도 하나의 R_10a로 치환 또는 비치환된 C₁-C₃₀헤테로시클릭 그룹이고, In Formula 31, L ₃₁ is a single bond, double bond, *-N(R _35a )-*', *-B(R _35a )-*', *-P(R _35a )-*', *-C (R _35a )(R _35b )-*', *-Si(R _35a )(R _35b )-*', *-Ge(R _35a )(R _35b )-*', *-S-*', * -Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C (R _35a )=*', *=C(R _35a )-*', *-C(R _35a )=C(R _35b )-*', *-C(=S)-*', *-C

A C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,

적어도 하나의 R_10a로 치환 또는 비치환된 C₅-C₃₀카보시클릭 그룹 또는 적어도 하나의 R_10a로 치환 또는 비치환된 C₁-C₃₀헤테로시클릭 그룹이고, L ₃₂ is a single bond, double bond, *-N(R _36a )-*', *-B(R _36a )-*', *-P(R _36a )-*', *-C(R _36a )( R _36b )-*', *-Si(R _36a )(R _36b )-*', *-Ge(R _36a )(R _36b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R _36a )= *', *=C(R _36a )-*', *-C(R _36a )=C(R _36b )-*', *-C(=S)-*', *-C

A C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,

적어도 하나의 R_10a로 치환 또는 비치환된 C₅-C₃₀카보시클릭 그룹 또는 적어도 하나의 R_10a로 치환 또는 비치환된 C₁-C₃₀헤테로시클릭 그룹이고, L ₃₃ is a single bond, double bond, *-N(R _37a )-*', *-B(R _37a )-*', *-P(R _37a )-*', *-C(R _37a )( R _37b )-*', *-Si(R _37a )(R _37b )-*', *-Ge(R _37a )(R _37b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R _37a )= *', *=C(R _37a )-*', *-C(R _37a )=C(R _37b )-*', *-C(=S)-*', *-C

A C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _10a ,

적어도 하나의 R_10a로 치환 또는 비치환된 C₅-C₃₀카보시클릭 그룹 또는 적어도 하나의 R_10a로 치환 또는 비치환된 C₁-C₃₀헤테로시클릭 그룹이다.L ₃₄ is a single bond, double bond, *-N(R _38a )-*', *-B(R _38a )-*', *-P(R _38a )-*', *-C(R _38a )( R _38b )-*', *-Si(R _38a )(R _38b )-*', *-Ge(R _38a )(R _38b )-*', *-S-*', *-Se-*' , *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R _38a )= *', *=C(R _38a )-*', *-C(R _38a )=C(R _38b )-*', *-C(=S)-*', *-C

It is a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ -C ₃₀ heterocyclic group substituted or unsubstituted with at least one R _10a .

In Formula 31, n31 to n34 are independently integers of 0 to 5, and at least 3 of n31 to n34 are independently integers of 1 to 5.

In Formula 31, when n31 is 0, L ₃₁ does not exist, when n32 is 0, L ₃₂ does not exist, when n33 is 0, L ₃₃ does not exist, and when n34 is 0, L ₃₄ does not exist. exist.

In Formula 31, when n31 is 2 or more, 2 or more L ₃₁ 's are the same or different from each other, when n32 is 2 or more, 2 or more L ₃₂ 's are the same or different from each other, and when n33 is 2 or more, 2 or more L ₃₃ 's are the same or different from each other. different, and when n34 is 2 or more, 2 or more L _34s are the same or different from each other.

In Formula 31, R ₃₁ to R ₃₄ , R _35a , R _35b , R _36a , R _36b , R _37a , R _37b , R _38a and R _38b are each independently selected from hydrogen, deuterium, -F, -Cl, - Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted Substituted 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 hetero Cycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₇ -C ₆₀ arylalkyl 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 C ₂ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ).

According to one embodiment, R ₃₁ to R ₃₄ , R _35a , R _35b , R _36a , R _36b , R _37a , R _37b , R _38a , and R _38b are each independently selected from hydrogen, deuterium, -F, -Cl , -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group (CN), nitro group, amino group, C ₁ -C ₂₀ alkyl group , or C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group (CN), nitro group, amino group , and a C ₁ -C ₂₀ alkyl group substituted with at least one of a phenyl group, or a C ₁ -C ₂₀ alkoxy group; or

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH _2, cyano group (CN), nitro group, amino group , C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, flu Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group substituted or unsubstituted with at least one of orenyl group, phenanthrenyl group, and anthracenyl group. It may be a til group, a fluorenyl group, a phenanthrenyl group, or an anthracenyl group.

According to one embodiment, the phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 31-1 or Chemical Formula 31-2:

<Formula 31-1>

<Formula 31-2>

In Formula 31, b31 to b34 are independently integers from 0 to 20.

In Formula 31, two or more of b31 R ₃₁ are optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group with at least one R _10a or at least one R _10a . may form a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

b2 or more of the 32 R _32s are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ - substituted or unsubstituted with at least one R _10a C ₃₀ can form a heterocyclic group,

b2 or more of the 33 R _33s are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ - substituted or unsubstituted with at least one R _10a C ₃₀ can form a heterocyclic group,

b2 or more of the 34 R _34s are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10a or a C ₁ - substituted or unsubstituted with at least one R _10a C ₃₀ may form a heterocyclic group.

Two or more of R ₃₁ to R ₃₄ , R _35a , R _35b , R _36a , R _36b , R _37a , R _37b , R _38a , and R _38b are optionally combined with each other and substituted or absent with at least one R _10a It may form a substituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group with at least one R _10a ,

The description of R _10a is the same as the description of R ₃₁ above.

In formulas 31-1 and 31-2,

_{M 31 , CY 32 , CY 33 , CY 34 , _} The information regarding is the same as described in this specification,

R ₃₁₁ to R ₃₁₇ are independent of each other and are the same as the description for R ₃₁ in this specification.

According to one embodiment, in Formulas 31-1 and 31-2, R ₃₁₁ to R ₃₁₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -SF ₅ , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salts thereof, sulfonic acid group or salts thereof, or phosphoric acid group or salts thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -SF ₅ , hydroxyl group, cyano group , a _C 1 -C 20 alkyl group, _or a C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted with a nitro group, amidino group, hydrazine group, hydrazone group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -SF ₅ , hydroxyl group, cyano group , nitro group, amidino group, hydrazine group, hydrazone group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group or any combination thereof, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₆ -C ₆₀ aryl group, C ₇ -C ₆₀ arylalkyl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , substituted or unsubstituted C ₂ -C ₆₀ heteroarylalkyl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ );

For example, in Formulas 31-1 and 31-2, at least one of R ₃₁₁ to R ₃₁₇ is,

C, which is at least one substituted or unsubstituted with methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, phenyl group, cumyl group, or a combination thereof It may include a ₁ -C ₂₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₇ -C ₆₀ arylalkyl group.

According to another embodiment, the phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 51:

<Formula 51>

M ₅₁ (L ₅₁ ) _n51 (L ₅₂ ) _n52

In Formula 51, M ₅₁ is a transition metal.

For example, M ₅₁ may be a 1-period transition metal, a 2-period transition metal, or a 3-period transition metal.

As another example, M ₅₁ is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium. (Tm) or rhodium (Rh).

According to one embodiment, M ₅₁ may be Ir, Pt, Os, or Rh.

In Formula 51, L ₅₁ may be a ligand represented by Formula 51A below, and L ₅₂ may be a ligand represented by Formula 51B below:

<Formula 51A> <Formula 51B>

　　　　　　　　

For descriptions of Formulas 51A and 51B, refer to the descriptions herein, respectively.

In Formula 51, n51 is 1, 2, or 3, and when n51 is 2 or more, two or more L ₅₁ 's may be the same or different from each other.

In Formula 51, n52 is 0, 1, or 2, and when n52 is 2, the two L ₅₂ 's may be the same or different from each other.

In Formula 51, the sum of n51 and n52 may be 2 or 3. For example, the sum of n51 and n52 may be 3.

According to one embodiment, in Formula 51, i) M ₅₁ is Ir, n51 + n52 is 3; or ii) M ₅₁ may be Pt, and n51 + n52 may be 2.

According to another embodiment, in Formula 51, M ₅₁ may be Ir, and i) n51 may be 1 and n52 may be 2, or ii) n51 may be 2 and n52 may be 1.

In Formula 51, L ₅₁ and L ₅₂ may be different from each other.

In Formulas 51A and 51B, Y ₅₁ to Y ₅₄ may each independently be C or N. For example, each of Y ₅₁ and Y ₅₃ may be N, and each of Y ₅₂ and Y ₅₄ may be C.

In Formulas 51A and 51B, CY ₅₁ to CY ₅₄ may independently be a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

For example, CY ₅₁ to CY ₅₄ are independently of each other: i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) two or more fourth rings are condensed with each other. Condensed condensed rings or v) condensed rings in which one or more third rings and one or more fourth rings are condensed with each other,

The third ring is a cyclopentane group, cyclopentene group, furan group, thiophene group, pyrrole group, silole group, borole group, phosphole group, low mole group, selenophene group, oxazole group, oxadiazole group, oxa a triazole group, a thiazole group, a thiadiazole group, a thitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azacylol group,

The fourth ring is an adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, and pyridazine group. Or it may be a triazine group.

As another example, in Formulas 51A and 5B, rings CY ₁ to CY ₄ are each independently selected from a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, Triphenylene group, pyrene group, chrysen group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, silol group, borole group, phosphole group, low mole group, selenophen group, indene group, indole group, benzofuran group, benzothiophene group, benzosilol group, benzoborole group, benzophosphole group, benzolowmole group , benzoselenophen group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, dibenzoborole group, dibenzophosphole group, dibenzogermol group, dibenzoselenophen group, benzofluorene group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzosilol group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermol group, Naphthobenzoselenophene group, dibenzofluorene group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthosilol group, dinaphtoborole group, dinaphthophosphole group, dinaphthogermol group, dinaphthoselenophen group, indenophenanthrene group, indolophenanthrene group, phenanthrobenzofuran group, phenanthrobenzothiophene group, phenanthrobenzosilol group, phenanthrobenzoborole group, phenanthrobenzophosphole group, phenanthrobenzogermol group, phenanthrobenzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5, 5-dioxide group, azaindene group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzosilol group, azabenzoborole group, azabenzophosphole group, azabenzogermol group, azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilol group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermole group, Azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzosilol group, azanaphthobenzoborole group, azanaf Tobenzophosphole group, azanaphthobenzogermol group, azanaphthobenzoselenophene group, azadibenzofluorene group, azadibenzocarbazole group, azadinapthofuran group, azadinapthothiophene group, azadi Naphthosilol group, azadinapthoborole group, azadinapthophosphole group, azadinapthogermole group, azadinapthoselenophen group, azaindenophenanthrene group, azaindophenanthrene group, azaphenanthrobenzo Furan (phenanthrobenzofuran) group, azaphenanthrobenzothiophene group, azaphenanthrobenzosilole group, azaphenanthrobenzoborole group, azaphenanthrobenzophosphole group, azaphenanthrobenzogermol group, azape Nanthrobenzoselenophene group, azadibenzothiophene 5-oxide group, aza9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, Pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, benzoquinoline group, benzoisoquinoline group, benzoquinoxaline group, benzoquinazoline group, phenanthroline group, phenanthridine group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, azacylol group, aza Borol group, azaphospol group, azazermol group, azaselenophen group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzoxadiazole group, benzothiadiazole group, pyridinopyrrole group, pyridinopyrazole group, pyridinoimidazole group, pyridinooxazole group, pyridinoisoxazole group, pyridinothiazole group, pyridinoimidazole group Dinoisothiazole group, pyridinooxadiazole group, pyridinothiadiazole group, pyrimidinopyrrole group, pyrimidinopyrazole group, pyrimidinoimidazole group, pyrimidinoxazole group, pyrimidinoi genus sazole group, pyrimidinothiazole group, pyrimidinoisothiazole group, pyrimidinooxadiazole group, pyrimidinothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7, 8-tetrahydroisoquinoline) group, 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline), adamantane group, norbornane group, norbornene group, It may be a benzene group fused with a cyclohexane group, a benzene group fused with a norbornane group, a pyridine group fused with a cyclohexane group, or a pyridine group fused with a norbornane group.

For example, CY ₅₁ and CY ₅₃ may be different from each other.

As another example, CY ₅₂ and CY ₅₄ may be different from each other.

As another example, each of CY ₅₁ to CY ₅₄ may be different from each other.

In Formulas 51A and 51B, R ₅₁ to R ₅₄ are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amine Dino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkene Nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₁ -C ₆₀ alkylthio 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 hetero Aryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )( Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or - It may be P(Q ₈ )(Q ₉ ). For descriptions of Q ₁ to Q ₉ , refer to what is described in the present specification.

According to one embodiment, in Formulas 51A and 51B, R ₅₁ to R ₅₄ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , phosphoric acid group or a salt thereof, -SF ₅ , C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group or C ₁ -C ₂₀ alkylthio group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo [2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ Alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbonanyl group, (C ₁ -C ₂₀ alkyl)norbornenyl group, (C ₁ -C ₂₀ alkyl) Cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group , a C ₁ -C 20 alkyl group, a C ₁ -C ₂₀ alkoxy _group , or a C ₁ -C ₂₀ alkylthio group substituted with a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, (phenyl)C ₁ -C ₁₀ alkyl group, C ₁ - C ₂₀ Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1 .1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbonanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group , phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group. group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyrida Zinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthrolinyl group , benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzooxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofura Nyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any of them. Substituted or unsubstituted by a combination of cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group , fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazole Diary group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, Isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoyl group Oxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopy Ridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group; or

-Ge(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) ) or -P(Q ₈ )(Q ₉ );

Q ₁ to Q ₉ are independently of each other,

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

Substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group, or naphthyl group.

According to another embodiment, R ₅₁ to R ₅₄ are independently of each other,

hydrogen, deuterium, -F, or cyano group;

Deuterium, cyano group, C ₃ -C ₁₀ cycloalkyl group, deuterated C ₃ -C ₁₀ cycloalkyl group, fluorinated C ₃ -C ₁₀ cycloalkyl group, (C ₁ -C ₂₀ alkyl)C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, deuterated C ₁ -C ₁₀ heterocycloalkyl group, fluorinated C ₁ -C ₁₀ heterocycloalkyl group, (C ₁ -C ₂₀ alkyl)C ₁ -C ₁₀ heterocycloalkyl group, phenyl group, deuterated phenyl group , fluorinated phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C ₁ -C ₂₀ alkyl)biphenyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, fluorinated Dibenzofuranyl group, (C ₁ -C ₂₀ alkyl)dibezofuranyl group, dibenzothiophenyl group, deuterated dibenzothiophenyl group, fluorinated dibenzothiophenyl group, (C ₁ -C ₂₀ alkyl)dibenzothiophenyl group, or C ₁ -C ₂₀ alkyl group substituted or unsubstituted by any combination thereof;

Deuterium, cyano group, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, deuterated C ₁ -C ₂₀ alkoxy group, fluorinated C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, deuterated C ₃ -C ₁₀ cycloalkyl group, fluorinated C ₃ -C ₁₀ cycloalkyl group, (C ₁ -C ₂₀ alkyl)C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, deuterated C ₁ -C ₁₀ heterocycloalkyl group, fluorinated C ₁ -C ₁₀ heterocycloalkyl group, (C ₁ -C ₂₀ alkyl)C ₁ -C ₁₀ heterocycloalkyl group, phenyl group, deuterated Phenyl group, fluorinated phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C ₁ -C ₂₀ alkyl)biphenyl group, dibenzofuranyl group, deuterated dibenzofuranyl group, Fluorinated dibenzofuranyl group, (C ₁ -C ₂₀ alkyl)dibezofuranyl group, dibenzothiophenyl group, deuterated dibenzothiophenyl group, fluorinated dibenzothiophenyl group, (C ₁ -C ₂₀ alkyl)dibenzothiophenyl group, or a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or a biphenyl group, substituted or unsubstituted by any combination thereof; or

-Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

In Formulas 51A and 51B, b51 to b54 each represent the number of R ₅₁ to R ₅₄ and may independently be an integer of 0 to 20. When b51 is 2 or more, two or more R ₅₁ 's are the same as or different from each other, when b52 is 2 or more, two or more R ₅₂ 's are the same as or different from each other, and when b53 is 2 or more, two or more R ₅₃ 's are the same or different from each other. , when b54 is 2 or more, 2 or more R ₅₄ may be the same or different from each other. For example, b51 to b54 may independently be integers from 0 to 8.

According to one embodiment, the phosphorescent dopant may be any one of the following compounds P1 to P52:

When the phosphorescent dopant is selected from compounds P1 to P52, formation of an exciplex with the above-described host compound may be facilitated. For example, the phosphorescent dopant contains a bulky substituent (eg, tert-butyl group, Q-pyl group, etc.) and thus has an energy level close to the host compound, making it easy to form an exciplex. In the case of the phosphorescent dopant, the gap between the LUMO (Lowest Occupied Molecular Orbital) level of the ET (electron transporting) host and the HOMO (Highest Occupied Molecular Orbital) level of the phosphorescent dopant is reduced, thereby favoring exiplex formation.

fluorescent dopant

According to one embodiment, the light-emitting layer may further include a fluorescent dopant. For example, the fluorescent dopant is a thermally activated delayed fluorescence dopant and may be a blue dopant.

The fluorescent dopant has a difference between the triplet energy level and the singlet energy level of 0.4 eV or less.

For example, the fluorescent dopant is a thermally activated delayed fluorescence dopant and may be a blue dopant.

According to one embodiment, the fluorescent dopant may be a light-emitting emitter that can emit light by transitioning to the ground state after receiving exciton from the exciplex of the host and phosphorescent dopant according to one embodiment of the present invention.

According to one embodiment, the fluorescent dopant may be a compound represented by the following Chemical Formula 41:

<Formula 41>

In Formula 41,

Z is B or N,

CY ₄₁ to CY ₄₃ are independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

L ₄₁ is *-N(R ₄₄ )-*', *-B(R ₄₄ )-*', *-P(R ₄₄ )-*', *-C(R ₄₄ )(R ₄₅ )-*' , *-Si(R ₄₄ )(R ₄₅ )-*', *-Ge(R ₄₄ )(R ₄₅ )-*', *-O-*', *-S-*', *-Se-* ', *-C(=O)-*', or *-S(=O) ₂ -*',

L ₄₂ is *-N(R ₄₆ )-*', *-B(R ₄₆ )-*', *-P(R ₄₆ )-*', *-C(R ₄₆ )(R ₄₇ )-*' , *-Si(R ₄₆ )(R ₄₇ )-*', *-Ge(R ₄₆ )(R ₄₇ )-*', *-O-*', *-S-*', *-Se-* ', *-C(=O)-*', or *-S(=O) ₂ -*',

L ₄₃ is *-N(R ₄₈ )-*', *-B(R ₄₈ )-*', *-P(R ₄₈ )-*', *-C(R ₄₈ )(R ₄₉ )-*' , *-Si(R ₄₈ )(R ₄₉ )-*', *-Ge(R ₄₈ )(R ₄₉ )-*', *-O-*', *-S-*', *-Se-* ', *-C(=O)-*', or *-S(=O) ₂ -*',

n41 to n43 are independently 0 or 1,

If n41 is 0, L ₄₁ does not exist, if n42 is 0, L ₄₂ does not exist, and if n43 is 0, L ₄₃ does not exist,

R ₄₁ to R ₄₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, car Boxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ - C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₇ -C ₆₀ arylalkyl 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 C ₂ - C ₆₀ heteroarylalkyl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ ),

b41 to b43 are independently integers from 1 to 20,

b2 or more of 41 R ₄₁ are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10b or a substituted or unsubstituted group with at least one R _10b C ₁ -C ₃₀ can form a heterocyclic group,

b2 or more of the 42 R _42s are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10b or a substituted or unsubstituted group with at least one R _10b C ₁ -C ₃₀ can form a heterocyclic group,

Two or more of b43 R ₄₃ are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group substituted or unsubstituted with at least one R _10b or a substituted or unsubstituted group with at least one R _10b C ₁ -C ₃₀ can form a heterocyclic group,

Two or more of R ₄₁ to R ₄₉ are optionally combined with each other to form a C ₅ -C ₃₀ carbocyclic group unsubstituted or substituted with at least one R _10b or C ₁ unsubstituted or substituted with at least one R _10b -C ₃₀ can form a heterocyclic group,

For the description of R _10b , refer to the description of R ₄₁ ,

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

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ) , -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ ) (Q ₁₉ ) or a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group substituted with any combination thereof;

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, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthi group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge( C ₃ - substituted with Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ) or any combination thereof. C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) or -P(=O)(Q ₃₈ )(Q ₃₉ );

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted Substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ - C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group; Or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

According to one embodiment, R ₄₁ to R ₄₉ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group (CN), nitro group, amino group, C ₁ -C ₆₀ alkyl group, or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group (CN), nitro group, amino group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluo a C ₁ -C ₆₀ alkyl group, or a C ₁ -C ₆₀ alkoxy group substituted with at least one of a lanthenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group (CN), nitro group, amino group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexane Syl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyridine Midinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolyl group Nyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group substituted or unsubstituted with at least one of benzofuranyl group, dibenzothiophenyl group, and carbazolyl group. , naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group. , thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinine Nolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxa It may be a zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, or carbazolyl group.

According to one embodiment, Formula 41 may be selected from the following Formulas 41-1 to 41-8:

<Formula 41-1>

<Formula 41-2>

<Formula 41-3>

<Formula 41-4>

<Formula 41-5>

<Formula 41-6>

<Formula 41-7>

<Formula 41-8>

<Formula 41-9>

In formulas 41-1 to 41-9,

Z ₁ and Z ₂ each refer to the description of Z in Formula 41,

Y ₄₁ and Y ₄₂ each refer to the description of L ₄₁ in Formula 41,

Y ₄₄ and Y ₄₅ refer to the description of Y ₄₁ and Y ₄₂ in Formula 41, respectively,

R ₄₁₁ refers to the description of R ₄₁ in Formula 41, R ₄₂₁ refers to the description of R ₄₂ in Formula 41, R _{431 and} R ₄₃₂ each refer to the description of R ₄₃ in Formula 41, R ₄₄₁ refers to the description of R ₄₁ in Formula 41, R ₄₅₁ refers to the description of R ₄₂ in Formula 41, and R ₄₆₁ refers to the description of R ₄₃ in Formula 41,

a411 is an integer selected from 0 to 4,

a421 is an integer selected from 0 to 3,

a431 is an integer selected from 0 to 4,

a441 is an integer selected from 0 to 4,

a451 is an integer selected from 0 to 3,

a461 is an integer selected from 0 to 4.

According to one embodiment, the fluorescent dopant may be selected from the following compounds D1 to D30:

According to one embodiment, the fluorescent dopant may be included in the light emitting layer in an amount of 0 to 5% by weight.

[Hole transport region (12)]

A hole transport region 12 is disposed between the first electrode 11 and the light emitting layer 15 of the organic light emitting device 10.

The hole transport region 12 may have a single-layer or multi-layer structure.

For example, the hole transport region 12 includes a hole injection layer, a hole transport layer, a hole injection layer/hole transport layer, a hole injection layer/first hole transport layer/second hole transport layer, and a hole injection layer/first hole transport layer/first hole transport layer. 2 It may have a structure of hole transport layer/electron blocking layer, hole transport layer/middle layer, hole injection layer/hole transport layer/middle layer, hole transport layer/electron blocking layer, or hole injection layer/hole transport layer/electron blocking layer.

The hole transport region 12 may include any compound having hole transport properties.

The hole transport region 12 may include a heterocyclic compound represented by Formula 1 herein. For example, the heterocyclic compound may be included in a hole transport layer, a hole transport layer, an electron blocking layer, or any combination thereof in the hole transport region.

For example, the hole transport region 12 may include an amine-based compound.

According to one embodiment, the hole transport region 12 is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid: polyaniline/camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), compounds represented by the formula 201 to: It may include one of the compounds represented by Formula 205, or any combination thereof:

<Formula 201>

<Formula 202>

<Formula 203>

<Formula 204>

<Formula 205>

In formulas 201 to 205,

L ₂₀₁ to L ₂₀₉ are each independently selected from *-O-*', *-S-*', a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group, or a substituted or unsubstituted C ₁ -C ₆₀ hetero It is a cyclic group,

xa1 to xa9 are independently integers from 0 to 5,

R ₂₀₁ to R ₂₀₆ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or 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, or substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. , and the two adjacent groups between R ₂₀₁ and R ₂₀₆ may optionally be connected to each other through a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

for example,

The L ₂₀₁ to L ₂₀₉ are deuterium, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, triphenyl group. Substituted or unsubstituted with a nyl group, biphenyl group, terphenyl group, tetraphenyl group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), or any combination thereof, benzene group, hepthalene group, indene group, naphthalene group , azulene group, heptalene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentacene group, hexacene group, pentacene group, rubisene group, corogen group. , ovalen group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group ophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group or tri It may be an indorobenzene group,

xa1 to xa9 are independently 0, 1, or 2,

R ₂₀₁ to R ₂₀₆ are independently of each other, 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 , -F substituted phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group , dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, penta Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofura Nyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), or substituted or unsubstituted with any combination thereof, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, Isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, indenocarbazolyl group, indolo It is a carbazolyl group, benzofurocarbazolyl group, or benzothienocarbazolyl group,

Q ₁₁ to Q ₁₃ and Q ₃₁ to Q ₃₃ may each independently be 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.

According to one implementation, the hole transport region 12 may include a carbazole-containing amine-based compound.

According to another embodiment, the hole transport region 12 may include a carbazole-containing amine-based compound and a carbazole-free amine-based compound.

The carbazole-containing amine compound includes, for example, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, It may include a compound represented by Formula 201, further comprising at least one of an indolocarbazole group, a benzofurocarbazole group, and a benzothienocarbazole group.

The carbazole-free amine-based compound, for example, does not contain a carbazole group, and includes a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, and indenocarbazole. It may include a compound represented by formula 201, comprising at least one of the group, indolocarbazole group, benzofurocarbazole group and benzothienocarbazole group.

According to another embodiment, the hole transport region 12 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

According to one embodiment, the hole transport region 12 may include a compound represented by the following formula 201-1, 202-1, or 201-2, or any combination thereof:

<Formula 201-1>

<Formula 202-1>

<Formula 201-2>

For descriptions of L ₂₀₁ to L ₂₀₃ , L ₂₀₅ , xa1 to xa3, xa5, R ₂₀₁ and R _{202 in the above formulas 201-1, 202-1 and 201-2} , refer to the description in the specification, respectively, and R ₂₁₁ to R ₂₁₃ 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, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, naphthyl group, fluorenyl group, spiro-bifluorenyl group , dimethylfluorenyl group, diphenylfluorenyl group, triphenylenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothio It may be a phenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, or pyridinyl group.

For example, the hole transport region 12 may include one of the following compounds HT1 to HT39, or any combination thereof:

Meanwhile, the hole transport region 12 of the organic light emitting device 10 may further include p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 is composed of a matrix (for example, at least one of the compounds represented by Formulas 201 to 205) and p contained in the matrix. -Can have a structure containing dopants. The p-dopant may be doped uniformly or non-uniformly in the hole transport region 12.

According to one embodiment, the LUMO energy level of the p-dopant may be -3.5 eV or less.

The p-dopant may include a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.

For example, the p-dopant is,

Quinone derivatives such as TCNQ (Tetracyanoquinodimethane), F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane), F6-TCNNQ, etc.;

metal oxides such as tungsten oxide and molybdenum oxide;

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

A compound represented by the following formula 221; or

any combination thereof;

May include:

<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, or 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, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, wherein at least one substituent among R ₂₂₁ to R ₂₂₃ is a cyano group; -F; -Cl; -Br; -I; C ₁ -C ₂₀ alkyl group substituted with -F; C ₁ -C ₂₀ alkyl group substituted with -Cl; C ₁ -C ₂₀ alkyl group substituted with -Br; C ₁ -C ₂₀ alkyl group substituted with -I; or any combination thereof.

The compound represented by Formula 221 may include, for example, the following compound HT-D2:

The thickness of the hole transport region 12 may be from about 100 Å to about 10000 Å, for example, from about 400 Å to about 2000 Å, and the thickness of the light emitting layer 15 may be from about 100 Å to about 3000 Å, for example from about 300 Å. It may be about 1000Å. When the thickness of the hole transport region 12 and the light emitting layer 15 satisfies the range described above, satisfactory hole transport characteristics and/or light emission characteristics can be obtained without a substantial increase in driving voltage.

The hole transport region 12 may further include a buffer layer.

The buffer layer may serve to increase efficiency by compensating for the optical resonance distance according to the wavelength of light emitted from the light emitting layer.

The hole transport region 12 may further include an electron blocking layer. The electron blocking layer may comprise known materials such as mCP or DBFPO:

[Electron transport region (17)]

An electron transport region 17 is disposed between the light emitting layer 15 and the second electrode 19 of the organic light emitting device 10.

The electron transport region 17 may have a single-layer or multi-layer structure.

For example, the electron transport region 17 may be an electron transport layer, an electron transport layer/electron injection layer, a buffer layer/electron transport layer, a hole blocking layer/electron transport layer, a buffer layer/electron transport layer/electron injection layer, or a hole blocking layer/electron transport layer/ It may have the structure of an electron injection layer. The electron transport region 17 may further include an electronic control layer.

The electron transport region 17 may include a heterocyclic compound represented by Formula 1 herein. For example, the heterocyclic compound may be included in a buffer layer of the electron transport region.

The electron transport region 17 may include a known electron transport material.

The electron transport region 17 (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer among the electron transport regions) includes at least one electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group. Metal-free compounds may be included. For a description of the electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, refer to the description herein.

For example, the electron transport region 17 may include a compound represented by the following formula 601.

<Formula 601>

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

In the above formula 601,

Ar ₆₀₁ and L ₆₀₁ are each independently a C ₅ -C ₆₀ carbocyclic group unsubstituted _or substituted with at least one R _601a or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R 601a ego,

xe11 is 1, 2, or 3,

xe1 is an integer from 0 to 5,

R _601a and R ₆₀₁ are independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or 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, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₆₀₁ )(Q ₆₀₂ )(Q ₆₀₃ ), -C(=O)(Q ₆₀₁ ), -S(=O) ₂ (Q ₆₀₁ ) or -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 an integer from 1 to 5.

According to one embodiment, at least one of the xe11 Ar ₆₀₁ and the xe21 R ₆₀₁ may include an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group as described above.

According to one embodiment, rings Ar ₆₀₁ and L ₆₀₁ in Formula 601 are each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydra. Zino 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 ), -P(=O)(Q ₃₁ )(Q ₃₂ ), or any combination thereof, substituted or unsubstituted, benzene group, naphthalene group, fluorene group, spiro- Bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene 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, cinolin group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, tria It may be a sol group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group or azacarbazole group,

Q ₃₁ to Q ₃₃ may independently be 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.

In Formula 601, when xe11 is 2 or more, 2 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 the above formula 601-1,

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

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

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

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

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

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

According to another embodiment, in the formulas 601 and 601-1, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ are each independently selected from 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-bifluore Nyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, Pentacenyl 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, pyrimidi Nyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group , acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyridinyl group, Substituted or unsubstituted with a polyzopyrimidinyl group, azacarbazolyl group, or any combination thereof, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, Furanyl group, carbazolyl group, indoleyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinium Nyl 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 group, phenanthridinyl group, acridinyl group, phenanthrolyl group Nyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group or azacarba sleep diary; or

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

ego,

For descriptions of Q ₆₀₁ and Q ₆₀₂ , refer to what is described herein.

The electron transport region 17 may include one of the following compounds ET1 to ET36, or any combination thereof:

Alternatively, the electron transport region 17 may be BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , BAlq , TAZ (3-(Biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole), NTAZ, DBFPO, or any combination thereof. You can. For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include BCP or Bphen.

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

The thickness of the electron transport layer may be about 100Å to about 1000Å, for example, about 150Å to about 500Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region 17 (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.

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

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

The electron transport region 17 may include an electron injection layer that facilitates electron injection from the second electrode 19. The electron injection layer may directly contact the second electrode 19.

The electron injection layer has i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of a plurality of different materials, or iii) a multi-layer structure having a plurality of layers made of a plurality of different materials. You 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 include Li, Na, K, Rb, Cs, or any combination thereof. 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.

The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof.

The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

The alkali metal compound, alkaline earth metal compound, and rare earth metal compound are oxides, halides (e.g., fluoride, chloride, bromide, iodide, etc.) of the alkali metal, alkaline earth metal, and rare earth metal, or any of them. It may include a combination of .

The alkali metal compound is one of alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O, etc., one of alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or It may include any combination thereof. According to one embodiment, the alkali metal compound may include LiF, Li ₂ O, NaF, LiI, NaI, CsI, KI, or any combination thereof.

The alkaline earth metal compound is one of 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), or It may include any combination thereof. According to one embodiment, the alkaline earth metal compound may include BaO, SrO, CaO, or any combination thereof.

The rare earth metal compound may include YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , TbF ₃ , or any combination thereof. According to one embodiment, the rare earth metal compound may include YbF ₃ , ScF ₃ , TbF ₃ , YbI ₃ , ScI ₃ , TbI ₃ , or any combination thereof.

The alkali metal complex, alkaline earth metal complex, and rare earth metal complex include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and are coordinated to the metal ions of the alkali metal complex, alkaline earth metal complex, and rare earth metal complex. The ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, and hydroxydiphenyloxa. Diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof. You can.

The electron injection layer is composed of only 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 as described above. , may further include the above organic matter. 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 non-uniformly dispersed in the matrix made of the organic material.

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

[Second electrode (19)]

The second electrode 19 is disposed on the organic layer 10A as described above. The second electrode 19 may be a cathode, which is an electron injection electrode. In this case, materials for the second electrode 19 include metals, alloys, electrically conductive compounds, and combinations thereof having a low work function. (combination) can be used.

The second electrode 19 is lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In). ), magnesium-silver (Mg-Ag), ITO, IZO, or any combination thereof. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 19 may have a single-layer structure or a multi-layer structure having a plurality of layers.

[Explanation of terms]

As used herein, the C ₁ -C ₆₀ alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and the C ₁ -C ₆₀ alkylene group has the same structure as the C ₁ -C ₆₀ alkyl group. It means a divalent group with .

Examples of C ₁ -C ₆₀ alkyl group, C ₁ -C ₂₀ alkyl group and/or C ₁ -C ₁₀ alkyl group in the present specification include methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, and sec -butyl group. , isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, n -hexyl group, iso Hexyl group, sec -hexyl group, tert -hexyl group, n -heptyl group, isoheptyl group, sec -heptyl group, tert -heptyl group, n -octyl group, isooctyl group, sec -octyl group, tert -octyl group, Substituted or unsubstituted with n -nonyl group, isononyl group, sec -nonyl group, tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group, tert -decyl group, or any combination thereof, Methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, n -hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n -heptyl group, isoheptyl group, sec -heptyl group, tert -heptyl group, n -octyl group, isooctyl group, sec -octyl group, tert -octyl group, n -nonyl group, isononyl group, sec -nonyl group, tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group or tert -decyl group, etc. may be included.

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the chemical formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group, ethoxy group, A propoxy group, butoxy group, or pentoxy group may be included.

As used herein, the C ₂ -C ₆₀ alkenyl group has a structure containing one or more carbon-carbon double bonds in the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, butenyl group, etc. This is included. As used herein, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

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

As used herein, the C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and the C ₃ -C ₁₀ cycloalkylene group refers to 2 having the same structure as the C ₃ -C ₁₀ cycloalkyl group. means group.

Examples of C ₃ -C ₁₀ cycloalkyl groups in the present specification include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, and norbornanyl group. )(bicyclo[2.2.1]heptyl),bicyclo[1.1.1]pentyl,bicyclo[2.1.1]hexyl ( bicyclo[2.1.1]hexyl), bicyclo[2.2.2]octyl, etc. may be included.

As used herein, the C ₁ -C ₁₀ heterocycloalkyl group is a monovalent group having 1 to 10 carbon atoms containing at least one hetero atom selected from B, N, O, P, Si, S, Se, Ge and B as a ring-forming atom. It refers to a monocyclic group, and the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

Examples of C ₁ -C ₁₀ heterocycloalkyl groups in the present specification include silolanyl, silinanyl, tetrahydrofuranyl, and tetrahydro-2H-pyranyl. ), tetrahydrothiophenyl, etc. may be included.

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

As used herein, the C ₁ -C ₁₀ heterocycloalkenyl group is one having 1 to 10 carbon atoms including at least one hetero atom selected from B, N, O, P, Si, S, Se, Ge and B as a ring-forming atom. is a monocyclic group and has at least one double bond in the ring. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 2,3-dihydrofuranyl group, 2,3-dihydrothiophenyl group, and the like. As used herein, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

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

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

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

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

As used herein, a monovalent non-aromatic condensed heteropolycyclic group has two or more rings condensed with each other, and contains carbon as a ring-forming atom (for example, the number of carbon atoms may be 1 to 60). It refers to a monovalent group containing heteroatoms selected from B, N, O, P, Si, S, Se, Ge and B, and the entire molecule having non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, "ð electron-depleted nitrogen-containing C ₁ -C ₆₀ cyclic group" refers to a ring moiety with *-N=*' ₍ above ₎ * and *' are each a bonding site with a neighboring atom) as a cyclic group having 1 to 60 carbon atoms including at least one group, for example, a) a first ring, b) two or more first rings condensed with each other. A condensed ring, or c) one or more first rings and one or more second rings may be condensed rings.

In _the present specification, "ð electron-rich C ₃ -C ₆₀ cyclic group" refers to a ring-forming moiety with *-N=*' (where * and _* ' are each It is a cyclic group with 3 to 60 carbon atoms that does not include a bonding site with a neighboring atom, and may be, for example, a) a second ring or b) a condensed ring in which two or more second rings are condensed with each other.

As used herein, “C ₅ -C ₆₀ cyclic group” refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms, for example, a) a third ring or b) a group in which two or more third rings are condensed with each other. It may be a condensed ring.

As used herein, “C ₁ -C ₆₀ heterocyclic group” refers to a monocyclic or polycyclic group having 1 to 60 carbon atoms containing at least one heteroatom, for example, a) a fourth ring, b) two or more rings. It may be a condensed ring in which the fourth ring is condensed with each other, or c) a condensed ring in which one or more third rings and one or more fourth rings are condensed with each other.

In the present specification, the “first ring” refers to an imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, and triazine group. It may be a sol group, tetrazole group, oxadiazole group, triazine group or thiadiazole group.

In the present specification, the “second ring” may be a benzene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, or silol group.

In the present specification, the “third ring” refers to a cyclopentane group, cyclopentadiene group, indene group, adamantane group, norbornene group, bicyclo[1.1.1]pentane group, and bicyclo[2.1. It may be a 1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, or a benzene group.

As used herein, the “fourth ring” refers to a furan group, thiophene group, pyrrole group, silole group, oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, and isoxatriazole. group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thitriazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, aza It may be a silol group, a diazacylol group or a triazine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group or a triazine group.

For example, the electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, and a pyrazine group. group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, benzoquinoxaline group. , quinazoline group, cinolin group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, Triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilol group, acridine group or pyridopyrazine group.

For example, the electron-rich C ₃ -C ₆₀ cyclic group is a benzene group, a hepthalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group. , spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphtha. cenene group, phycene group, perylene group, pentacene group, hexacene group, pentaphene group, rubisene group, coronene group, ovalene group, pyrrole group, furan group, thiophene group, isoindole group, indole group , indene group, benzofuran group, benzothiophene group, benzosilol group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthosilol group, benzocarbazole group, dibenzocarbazole group, dibenzo Furan group, dibenzothiophene group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group, benzothienocarbazole group, benzosilolocarbazole group , triindolobenzene group, pyrrolophenanthrene group, furanophenanthrene group, thienophenanthrene group, benzonaphthofuran group, benzonaphthothiophene group, (indolo)phenanthrene group, (benzofurano) It may be a phenanthrene group, or a (benzothieno)phenanthrene group.

For example, the C ₅ -C ₆₀ carbocyclic group is a cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, Chrysen group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, indene group, fluorene group, 5,6,7,8-tetrahydro Isoquinoline (5,6,7,8-tetrahydroisoquinoline) group, 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group, adamantane group, norbornane It may be a (norbornane) group or a norbornene group.

For example, the C ₁ -C ₆₀ heterocyclic group is a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a silole group, a borole group, a phosphole group, a selenophene group, a low mole group, and a benzotine group. ophene group, benzofuran group, indole group, indene group, benzosilol group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, Dibenzosilol group, dibenzoborole group, dibenzophosphole group, dibenzoselenophen group, dibenzogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzoborole group, azabenzophosphopol group, azabenzoselenophene group, aza Benzogermole group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzoborole group, azadibenzophosphole group, azadibenzosele nophen group, azadibenzogermol group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, Pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadia It could be a group of pawns.

In this specification, each of the electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, the electron-excessive C ₃ -C ₆₀ cyclic group, the C ₅ -C ₆₀ cyclic group, and the C ₁ -C ₆₀ heterocyclic group, Depending on the chemical structure, it may be part of a condensed ring, or may be a monovalent, divalent, trivalent, tetravalent, pentavalent or hexavalent group.

In the present specification, the substituted ð electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, the substituted ð electron-rich C ₃ -C ₆₀ cyclic group, the substituted C ₅ -C ₆₀ cyclic group, and the substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₁ -C ₆₀ alkylene group, substituted C ₂ -C ₆₀ alkenylene group, substituted C ₂ -C ₆₀ alkynylene group, substituted C ₃ -C ₁₀ cycloalkylene group, Substituted C ₁ -C ₁₀ heterocycloalkylene 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 heterocondensed 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 cycloalke Nyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ The substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are independently of one another,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteroaryl group, -N(Q ₁₁ )(Q ₁₂ ), -Si (Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )( Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or substituted with any combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, or C ₁ - C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, 1 A non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ ) (Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any of them. Substituted or unsubstituted in combination, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent a non-aromatic condensed polycyclic group or a monovalent non-aromatic heterocondensed polycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ), or -P(Q ₃₈ )(Q ₃₉ ); or

any combination thereof;

It can be.

In this specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; amidino group; hydrazine group; hydrazone group; Carboxylic acid group or salt thereof; Sulfonic acid group or salt thereof; Phosphoric acid group or salt thereof; C ₁ -C ₆₀ alkyl group _substituted or unsubstituted _with deuterium, C 1 -C 60 alkyl group, C ₆ -C ₆₀ aryl group, or any combination thereof; 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 substituted or unsubstituted with deuterium, C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group, or _any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; monovalent non-aromatic condensed polycyclic group; Or it may be a monovalent non-aromatic heterocondensed polycyclic group.

For example, in the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently of each other,

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

Substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

It can be.

In this specification, “room temperature” refers to a temperature of approximately 25°C.

As used herein, “biphenyl group, terphenyl group, and tetraphenyl group” refers to a monovalent group in which 2, 3, or 4 phenyl groups are linked to each other through a single bond, respectively.

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present invention will be described in more detail through synthesis examples and embodiments, but the present invention is not limited to the following synthesis examples and embodiments. In the following synthesis example, in the expression "'B' was used instead of 'A'", the amount of 'B' used and the amount of 'A' used are the same on a molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of Compound 22

Compound 22 was synthesized according to the following reaction scheme.

(One) Synthesis of Intermediate 4

1-bromo-3-iodobenzene-2,4,5,6-d4 (1-bromo-3-iodobenzene-2,4,5,6-d4) (30 g, 123.7 mmol), (phenyl- d5) boronic acid (phenyl-d5)boronic acid (13 g, 103 mmol), Tetrakis(triphenylphosphine)palladium(0) (5.95 g, 5.15 mmol), Add sodium bicarbonate (21.6 g, 257 mmol), 400 mL of toluene, 100 mL of ethanol, and 100 mL of distilled water and heat at 120 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried with anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 4. (yield 70%)

LCMS (calculated value: 241.05, measured value (M+1): 242.08 m/z)

(2) Synthesis of Intermediate 5

Intermediate 4 (20.1 g, 45.2 mmol), Bis(pinacolato)diboron) (13.7 g, 54.2 mmol), Potassium acetate (11.1 g, 113 mmol), Bis(tri) Phenylphosphine)palladium(II) dichloride (Bis(triphenylphosphine)palladium(II) dichloride) (1.6 g, 2.3 mmol), add to 220 mL of toluene and heat at 130 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 5. (11.2 g, 38.7 mmol, yield 85%)

LCMS (calculated value: 289.22, measured value (M+1): 290.25 m/z)

(3) Synthesis of Intermediate 6

1-Bromo-3-iodobenzene (17.3 g, 60.9 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 ( 9H-carbazole-1,2,3,4,5,6,7,8-d8) (8.9 g, 50.8 mmol), Copper(I) iodide (4.8 g, 25.4 mmol), triphosphate Add Potassium phosphate (32.3 g, 152.4 mmol), Ethylenediamine (6.1 g, 101.6 mmol), and 250 mL of toluene and heat at 130 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 6. (11.6 g, 35.2 mmol, yield 70%)

LCMS (calculated value: 329.07, measured value (M+1): 330.09 m/z)

(4) Synthesis of Intermediate 7

Intermediate 6 (11.6 g, 35.2 mmol), Intermediate 5 (11.2 g, 38.7 mmol), Tetrakis(triphenylphosphine)palladium(0) (1.6 g, 1.4 mmol), Add sodium bicarbonate (12.2 g, 88 mmol), 135 mL of tetrahydrofuran, and 45 mL of distilled water and heat at 90 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 7. (10.3 g, 25.0 mmol, yield 71%)

LCMS (calculated value: 412.27, measured value (M+1): 413.25 m/z)

(5) Synthesis of Intermediate 8

Intermediate 7 (24.7 g, 60.5 mmol) and 600 mL of dimethylformamide were stirred at 0 degrees. While maintaining the temperature at 0 degrees, N-Bromosuccinimide (10.2 g, 57.5 mmol) dissolved in 50 mL of dimethylformamide was added dropwise and stirred at room temperature for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 8. (yield 88%)

LCMS (calculated value: 489.18, measured value (M+1): 490.18 m/z)

(6) Synthesis of compound 22

Intermediate 8 (27.8 g, 56.6 mmol), (9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.4 g, 59.4 mmol), Sodium tert-butoxide (Sodium tert- butoxide) (8.2 g, 84.9 mmol), Tris(dibenzylideneacetone)dipalladium(0) (2.1 g, 2.3 mmol), tri-tert-butylphosphine (Tri- tert-butylphosphine) (1.8 mL, 4.5 mmol), add to 280 mL of toluene and heat at 130 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried with anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and subjected to silica column to synthesize Compound 22. (yield 66%)

LCMS (calculated value: 584.38, measured value (M+1): 585.39 m/z)

Synthesis Example 2: Synthesis of Compound 98

Compound 98 was synthesized according to the following reaction scheme.

(One) Synthesis of Intermediate 12

When synthesizing intermediate 4, use 1,3-dibro instead of 1-bromo-3-iodobenzene-2,4,5,6-d4 (1-bromo-3-iodobenzene-2,4,5,6-d4) Intermediate 12 was synthesized using the same method as the synthesis of Intermediate 4 in Synthesis Example 1, except that 1,3-dibromo-2-fluorobenzene was used. (yield 47%)

LCMS (calculated value: 258.16, measured value (M+1): 259.18 m/z)

(2) Synthesis of Intermediate 13

Intermediate 12 (12g, 46.3 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (9H-carbazole-1,2,3,4,5,6,7, 8-d8) (8.76 g, 50.0 mmol) and cesium carbonate (24.4 g, 75.0 mmol) were added to 100 ml of N,N-dimethylformamide and stirred at 165 degrees for 20 hours. did. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize intermediate (13).

(3) Synthesis of intermediate 14

The intermediate 13 (25 g, 60.5 mmol) and 600 mL of dimethylformamide were stirred at 0 degrees. While maintaining the temperature at 0 degrees, N-Bromosuccinimide (10.2 g, 57.5 mmol) dissolved in 50 mL of dimethylformamide was added dropwise and stirred at room temperature for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and then subjected to silica column to synthesize Intermediate 14.

(4) Synthesis of compound 98

The intermediate 14 (27.8 g, 56.6 mmol), (9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.4 g, 59.4 mmol), sodium tert-butoxide (Sodium tert) -butoxide) (8.2 g, 84.9 mmol), Tris(dibenzylideneacetone)dipalladium(0) (Tris(dibenzylideneacetone)dipalladium(0)) (2.1 g, 2.3 mmol), tri-tert-butylphosphine (Tri -tert-butylphosphine) (1.8 mL, 4.5 mmol), add to 280 mL of toluene and heat at 130 degrees for 16 hours. After completion of the reaction, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate, dried with anhydrous magnesium sulfate (MgSO ₄ ), concentrated, and subjected to silica column to synthesize Compound 98.

LCMS (calculated value: 585.38, measured value (M+1): 586.40 m/z)

Example 1

A glass substrate on which a 1500 Å thick ITO (indium tin oxide) electrode (first electrode, anode) was formed was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate was ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum laminate.

Compound HT3 and compound HT-D2 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer with a thickness of 100 Å, and then compound HT3 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1300 Å. Then, mCP was deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å, thereby forming a hole transport region.

Compound P31 as a host and a dopant was co-deposited on the hole transport region at a weight ratio of 85:15 to form a 300Å thick light emitting layer. The host included a first host (Compound 22) and a second host (Compound E1), and the weight ratio of the first host and the second host was adjusted to 6:4.

BCP was vacuum deposited on the emitting layer to form a 100 Å thick hole blocking layer, and a 300 Å thick electron transport layer was formed by vacuum depositing compounds ET3 and Liq on the hole blocking layer. Liq was then deposited on the electron transport layer. An organic light emitting device was manufactured by depositing an electron injection layer with a thickness of 10 Å and forming a second Al electrode (cathode) with a thickness of 1200 Å on the electron injection layer.

Example 2 and Comparative Examples 1 and 2

An organic light-emitting device was manufactured using the same method as Example 1, except that the compound shown in Table 2 below was used instead of Compound 22 when forming the light-emitting layer.

Evaluation Example 1: Evaluation of characteristics of organic light-emitting device

For each of the organic light emitting devices manufactured in Examples 1 and 2 and Comparative Examples 1 and 2, the lifespan (T ₉₅ at 1,000 nit, hr) was measured using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The evaluation was performed, and the results are shown in Table 2. Lifespan (T ₉₅ ) is an evaluation of the time it takes for the luminance to reach 95% of the initial luminance of 100%. Example 1 was described in terms of lifespan relative to Comparative Example 1, and Example 2 was described in terms of relative lifespan (%) compared to Comparative Example 2.

host of luminescent layers dopant life span
(T ₉₅ ) first host 2nd host Example 1 10 E1 P31 198%
(Compared to Comparative Example 1) Comparative Example 1 C2 E1 P31 100% Example 2 54 E1 P31 162% (compared to Comparative Example 2) Comparative Example 2 C4 E1 P31 100%

From Table 2, it can be seen that the organic light emitting devices of Examples 1 and 2 have a lifespan improvement of up to 198% compared to Comparative Examples 1 and 2.

Example 3

A glass substrate on which a 1500 Å thick ITO (indium tin oxide) electrode (first electrode, anode) was formed was washed with distilled water ultrasonic waves. After washing with distilled water, the substrate was ultrasonic cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum laminate.

Compound HT3 and compound HT-D2 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer with a thickness of 100 Å, and then compound HT3 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1300 Å. Then, mCP was deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å, thereby forming a hole transport region.

A host, a phosphorescent dopant (compound P31), and a fluorescent dopant (compound D3) were co-deposited on the hole transport region at a weight ratio of 85:14:1 to form an emission layer with a thickness of 300 Å. The host included a first host (Compound 22) and a second host (Compound E1), and the weight ratio of the first host and the second host was adjusted to 6:4.

BCP was vacuum deposited on the emitting layer to form a 100 Å thick hole blocking layer, and a 300 Å thick electron transport layer was formed by vacuum depositing compounds ET3 and Liq on the hole blocking layer. Liq was then deposited on the electron transport layer. An organic light emitting device was manufactured by depositing an electron injection layer with a thickness of 10 Å and forming a second Al electrode (cathode) with a thickness of 1200 Å on the electron injection layer.

Example 4 and Comparative Examples 3 and 4

An organic light-emitting device was manufactured using the same method as Example 3, except that the compound in Table 3 below was used instead of Compound 22 when forming the light-emitting layer.

Evaluation Example 2: Evaluation of characteristics of organic light-emitting device

For each organic light emitting device manufactured in Examples 3 and 4 and Comparative Examples 3 and 4, the lifespan (T ₉₅ at 1,000 nit, hr) was measured using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The evaluation was performed, and the results are shown in Table 3. Lifespan (T ₉₅ ) is an evaluation of the time it takes for the luminance to reach 95% of the initial luminance of 100%. Example 3 was described in terms of lifespan relative to Comparative Example 3, and Example 4 was described in terms of relative lifespan (%) compared to Comparative Example 4.

host of luminescent layers Dopant in the emitting layer life span
(T ₉₅ ) first host 2nd host Phosphorescent dopant fluorescent dopant Example 3 10 E1 P31 D3 195%
(Compared to Comparative Example 3) Comparative Example 3 C2 E1 P31 D3 100% Example 4 54 E1 P31 D3 129%
(Compared to Comparative Example 4) Comparative Example 4 C4 E1 P31 D3 100%

From Table 3, it can be seen that the organic light emitting devices of Examples 3 and 4 have a lifespan improvement of up to 195% compared to Comparative Examples 3 and 4.

11: first electrode
12: Hole transport area
15: light-emitting layer
17: Electron transport area
19: second electrode

Claims (20)

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

In Formula 1A,
k1 is one of the integers from 1 to 5,
n1 is one of the integers from 1 to 3,
n2 is one of the integers from 0 to 3,
R ₁ to R ₄ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q _{3 )} (Q 4 )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),
R ₅ to R ₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),
d1, d2, d3, d5, and d6 are independently one of the integers from 0 to 4,
d4 is one of the integers from 0 to 3,
d7 is one of the integers from 0 to 5,
In Formula 1A, The moiety represented by is a group represented by one of the following formulas 5-1 to 5-9,

In formulas 5-1 to 5-9,
R ₅ to R ₇ are each the same as described above,
d75, d75' and d75" are independently one of the integers from 0 to 5,
d54, d64 and d64' are independently one of the integers from 0 to 4,
d53 is one of the integers from 0 to 3,
d52 is one of the integers from 0 to 2,
The heterocyclic compound represented by Formula 1 contains at least one deuterium,
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group. The substituent is,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group, substituted in any combination;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any combination thereof, substituted or unsubstituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group;
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or
any combination thereof;
ego,
Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; hydroxyl group; Cyano group; nitro group; amidino group; hydrazine group; hydrazone group; Carboxylic acid group or salt thereof; Sulfonic acid group or salt thereof; Phosphoric acid group or salt thereof; C ₁ -C ₆₀ alkyl group substituted _or unsubstituted _with deuterium, C 1 -C 60 alkyl group, C ₆ -C ₆₀ aryl group, or any combination thereof; 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 substituted or unsubstituted with deuterium, C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group, or _any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group. According to paragraph 1,
The heterocyclic compound represented by Formula 1A is a heterocyclic compound that satisfies at least one of the following conditions 1 to 7:
<Condition 1>
At least one of d1 R _1s is deuterium
<Condition 2>
At least one of d2 R _2s is deuterium
<Condition 3>
At least one of n1*d3 R _3s is deuterium
<Condition 4>
At least one of n1*d4 R _4s is deuterium
<Condition 5>
At least one of d5 R _5s is deuterium
<Condition 6>
At least one of k1*n2*d6 R _6s is deuterium
<Condition 7>
At least one of k1*d7 R _7s is deuterium. According to paragraph 1,
The heterocyclic compound represented by Formula 1A is a heterocyclic compound that satisfies at least one of the following conditions 1' to 7':
<Condition 1'>
All d1 R _1s are deuterium, and d1 is 4.
<Condition 2'>
All d2 R _2s are deuterium, and d2 is 4.
<Condition 3'>
All n1*d3 R _3s are deuterium, and d3 is 4.
<Condition 4'>
All n1*d4 R _4s are deuterium, and d4 is 3.
<Condition 5'>
All d5 R _5s are deuterium,
k1 is 1 and d5 is 4; or k1 is 2 and d5 is 3
<Condition 6'>
k1*n2*d6 R _6s are all deuterium, and d6 is 4
<Condition 7'>
All k1*d7 R _7s are deuterium, and d7 is 5. According to paragraph 1,
A heterocyclic compound represented by Formula 1A has a deuterium substitution rate of 10% or more. According to paragraph 1,
Wherein n1 is 1 or 2, a heterocyclic compound. According to paragraph 1,
In Formula 1A, The moiety represented by is a heterocyclic compound, which is a group represented by one of the following formulas 2-1 to 2-4:

In Formulas 2-1 to 2-4,
The descriptions of R ₃ , R ₄ , d3 and d4 are each the same as the description in paragraph 1,
* and *' are binding sites with neighboring atoms. According to paragraph 1,
In Formula 1A, The moiety represented by is a heterocyclic compound, which is a group represented by one of the following formulas 3-1 to 3-20:




In Formulas 3-1 to 3-20,
R ₁₁ to R ₁₄ are each the same as the description for R ₁ in clause 1,
R ₂₁ to R ₂₄ are each the same as the description for R ₂ in clause 1,
R ₃₁ to R ₃₈ are each the same as the description for R ₃ in clause 1,
R ₄₁ to R ₄₈ are each the same as the description for R ₄ in clause 1,
* is a bonding site with a neighboring atom. According to paragraph 1,
R ₁ to R ₄ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydra Alkenyl group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or Unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ), or -P(Q ₈ )(Q ₉ ),
The description of Q ₁ to Q ₉ is the same as that of paragraph 1. According to paragraph 1,
The heterocyclic compound represented by Formula 1 is a heterocyclic compound represented by one of the following formulas 1A-1 to 1A-12:


In formulas 1A-1 to 1A-12,
R ₁ to R ₅ are each the same as the description in paragraph 1,
d75, d75' and d75" are independently one of the integers from 0 to 5,
d14, d24, d34, d34', d54, d64 and d64' are independently one of the integers from 0 to 4,
d43, d43' and d53 are independently one of the integers from 0 to 3,
d52 is one of the integers from 0 to 2,
The heterocyclic compounds represented by Formulas 1A-1 to 1A-12 each contain at least one deuterium. Regarding paragraph 1:
The heterocyclic compound represented by Formula 1 is a heterocyclic compound represented by one of the following Formulas 1-1 to 1-106:

















In formulas 1-1 to 1-106,
At least one hydrogen is replaced with deuterium. first electrode;
second electrode; and
an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer;
Including,
An organic light-emitting device, wherein the organic layer contains at least one heterocyclic compound according to any one of claims 1 to 10. According to clause 11,
The organic layer 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 includes a hole injection layer, a hole transport layer, an electron blocking layer, an auxiliary layer, or any combination thereof,
The electron transport region is an organic light emitting device comprising a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. According to clause 11,
An organic light-emitting device wherein the heterocyclic compound is included in the light-emitting layer. According to clause 11,
An organic light-emitting device wherein the heterocyclic compound is included in the hole transport region. According to clause 12,
An organic light-emitting device wherein the heterocyclic compound is included in the electron transport region. According to clause 13,
An organic light-emitting device, wherein the light-emitting layer further includes a phosphorescent dopant. According to clause 16,
An organic light emitting device wherein the light emitting layer further includes a fluorescent dopant. According to clause 13,
The organic light-emitting device wherein the light-emitting layer further includes an electron-transporting host. According to clause 18,
The electron-transporting host is an organic light-emitting device comprising a cyano group, an electron-deficient nitrogen-containing C ₁ -C ₆₀ cyclic group, a group represented by one of the following formulas, or any combination thereof. An electronic device comprising the organic light emitting device of claim 11.