KR20190059224A - Composition, thin film and organic light emitting device including the same - Google Patents

Abstract

The present invention relates to a composition, a thin film including the same, and an organic light emitting device including the same. The composition of the present invention comprises: a first compound represented by chemical formula 1, A_11-L_11-A_12, a second compound represented by chemical formula 2, A_21-(L_21)_a21-A_22, and a third compound satisfying condition 1, 0 eV <= E_S1(C3) - E_T1(C3) <= 0.3 eV. Therefore, the organic light emitting device having the thin film can have low roll-off, high efficiency, and long lifetime at the same time.

Description

A thin film including the composition, and an organic light emitting device including the thin film and a thin film including the organic light emitting device,

A thin film including the composition, and an organic light emitting device including the same.

The organic light emitting device is a self light emitting type device, which has a wider viewing angle and superior contrast as well as a faster response time, superior luminance, driving voltage and response speed characteristics, .

According to an example, the organic light emitting element may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transporting region may be provided between the anode and the light emitting layer, and an electron transporting region may be provided between the light emitting layer and the cathode. The holes injected from the anode move to the light emitting layer via the hole transporting region, and electrons injected from the cathode move to the light emitting layer via the electron transporting region. The holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

A composition comprising a first compound, a second compound and a third compound, a thin film containing the composition, and an organic light emitting device comprising the thin film.

According to an aspect, there is provided a compound represented by Formula 1 below; A second compound represented by the following formula (2); And a third compound satisfying the following condition 1, wherein the first compound and the second compound are different from each other:

&Lt; Formula 1 >

A ₁₁ -L ₁₁ -A ₁₂

(2)

_{A 21 - (L 21) a21} -A 22

&Lt; Formula 10-1 > < EMI ID =

<Formula 11-1> Formula 11-2> Formula 11-3>

&Lt; Formula 20-1 > < EMI ID =

<Condition 1>

0 eV ≤ E _S1 (C3) - E _T1 (C3) ≤0.3 eV

In the above condition 1,

E _S1 (C3) is the lowest excited singlet energy level of said third compound;

E _T1 (C3) is the lowest excited triplet energy level of said third compound;

Where E _S1 (C3) and E _T1 (C3) are evaluated using a DFT method that is structurally optimized at the B3LYP / 6-31G (d, p) level;

Among the above general formulas (1) and (2)

A ₁₁ is a group represented by the above formula (10-1);

A ₁₂ is a group represented by the above formula (10-2);

L ₁₁ is a group represented by any one of formulas (11-1) to (11-3);

A ₂₁ is a group represented by any one of formulas (20-1) and (20-2);

A ₂₂ represents a group represented by the formula (20-1), a group represented by the formula (20-2), a phenyl group, a naphthyl group and a benzimidazolyl group; Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a halogen atom, A phenyl group, a naphthyl group and a benzimidazolyl group substituted with at least one member selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;

X ₂₁ is a single _{bond, C [(L 27) a27} -R 26] is selected from _{[(L 28) a28 -R 27} ], O and S;

X ₂₂ is _{N [(L 26) a26 -R} 25], C [(L 29) a29 -R 28] is selected from _{[(L 30) a30 -R 29} ], O and S;

L ₂₁ to L ₃₀ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Aromatic divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;

a21 to a30 are each independently selected from 0, 1, 2, 3, 4 and 5;

R _11a to R _11h , R _12a to R _12h , R _13a to R _13h and R ₂₁ to R ₂₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, (CN), 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, 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, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or non-monovalent unsubstituted aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3) , -N (Q ₁ ) (Q ₂ ) and -B (Q ₁ ) (Q ₂ ), and at least two of R ₂₁ to R ₂₉ may optionally combine to form a ring;

At least one of R _11a to R _11h , R _12a to R _12h and R _13a to R _13h is a cyano group;

b21, b22 and b24 are independently of each other selected from 1, 2, 3 and 4;

b23 is selected from 1, 2 and 3;

Q ₁ to Q ₃ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic , Biphenyl group and terphenyl group;

* And * are binding sites with neighboring atoms.

According to another aspect, a thin film comprising the composition is provided.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the thin film. Here, the thin film of the organic light emitting device may be a light emitting layer.

The organic light emitting device including the thin film including the first compound, the second compound, and the third compound may have low roll-off, high efficiency, and long life.

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

Said composition comprising: a first compound represented by the following formula (1); A second compound represented by the following formula (2); And a third compound satisfying the following condition 1, wherein the first compound and the second compound may be different from each other:

&Lt; Formula 1 >

A ₁₁ -L ₁₁ -A ₁₂

(2)

_{A 21 - (L 21) a21} -A 22

<Condition 1>

0 eV ≤ E _S1 (C3) - E _T1 (C3) ≤0.3 eV

Wherein, in the above condition 1, E _S1 (C3) is the lowest excited singlet energy level of the third compound; E _T1 (C3) is the lowest excited triplet energy level of the third compound.

Here, E _S1 (C3) and E _T1 (C3) are evaluated using a DFT method that is structurally optimized at the B3LYP / 6-31G (d, p) level. Specifically, E _S1 (C3) and E _T1 (C3) can be evaluated using a Gaussian program.

In the above formula (1), A ₁₁ is a group represented by the following formula (10-1); A ₁₂ is a group represented by the following formula (10-2):

&Lt; Formula 10-1 > < EMI ID =

In the above general formulas (10-1) and (10-2), R _11a to R _11h and R _12a to R _12h are described later, and * is a bonding site with neighboring atoms.

Wherein L ₁₁ is a group represented by any one of the following formulas (11-1) to (11-3):

<Formula 11-1> Formula 11-2> Formula 11-3>

The description of Formulas 11-1 to 11-3 and R _13a to R _13h will be described later, and * is a binding site with neighboring atoms.

For example, in Formula 1, L ₁₁ may be a group represented by Formula 11-1, but is not limited thereto.

R _11a to R _11h , R _12a to R _12h and R _13a to R _13h in the general formulas 10-1, 10-2 and 11-1 to 11-3 are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl , A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituent or a substituent Substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or 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, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero Import cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl tea, Unsubstituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic group, -Si (Q ₁₎ ( selected from _{Q 2) (Q 3),} -N (Q 1) (Q 2) and _{-B (Q 1) (Q 2} ) thereof;

At least one of R _11a to R _11h , R _12a to R _12h and R _13a to R _13h is a cyano group;

Q ₁ to Q ₃ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic , Biphenyl group and terphenyl group.

For example, in the above formulas 10-1, 10-2 and 11-1 to 11-3, one, two or three of R _11a to R _11h , R _12a to R _12h and R _13a to R _13h are Cyano group, but is not limited thereto.

As another example, in the general formulas (10-1), (10-2) and (11-1) to (11-3), R _11a to R _11h , R _12a to R _12h and R _13a to R _13h independently of one another are hydrogen, deuterium, An alkoxy group, a nitro group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with at least one selected from deuterium and cyano groups;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Heavy hydrogen, cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, pyrazinyl group, pyrimidinyl group, carbazole group A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group which are substituted with at least one selected from a dibenzofuranyl group and a dibenzothiophenyl group; , But is not limited thereto.

In another embodiment, R _11a to R _11h , R _12a to R _12h and R _13a to R _13h in the general formulas (10-1), (10-2) and (11-1) to (11-3) independently represent hydrogen, deuterium, An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group and a tert-butyl group;

An ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group and a tert-butyl group substituted with at least one selected from deuterium and cyano group;

A phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group and a pyrimidinyl group; And

Substituted with at least one member selected from the group consisting of hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec- , A phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group and a pyrimidinyl group; , But is not limited thereto.

According to one embodiment, A ₁₁ in the formula 1 is represented by the following formula 10-11, A ₁₂ is represented by the following formula 10-21, L ₁₁ is represented by the following formulas 11-15 to 11-22, 11- 27 to 11-34 and 11-37 to 11-40;

A ₁₁ is represented by any one of the following formulas 10-12 and 10-13, A ₁₂ is represented by any one of the following formulas 10-21 to 10-23, L ₁₁ is any one of the following formulas 11-11 to 11-40 Displayed as one; or

A ₁₁ is represented by the following formula 10-11, A ₁₂ is represented by any one of the following formulas 10-22 and 10-23, and L ₁₁ may be represented by any one of the following formulas 11-11 to 11-40, But are not limited to:

Of the above formulas 10-11 to 10-13, 10-21 to 10-23 and 11-11 to 11-40,

R _11c , R _11f , R _12c , R _12f and R _13a to R _13f are independently selected from the group consisting of hydrogen, deuterium, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, biphenyl group, A t-butyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with deuterium; And

Deuterium, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, pyrazinyl group, pyrimidinyl group, carbazole group, a dibenzo A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzofuranyl group which are substituted with at least one member selected from a furanyl group and a dibenzothiophenyl group; A dibenzothiophenyl group; &Lt; / RTI &gt;

* And * are binding sites with neighboring atoms.

According to another embodiment, A ₁₁ of Formula 1 is represented by Formula 10-11, A ₁₂ is represented by Formula 10-21, L ₁₁ is Formula 11-27 to 11-34, and 11- 37 to 11-40;

A ₁₁ is represented by any one of Formulas 10-12 and 10-13, A ₁₂ is represented by any one of Formulas 10-21 to 10-23, and L ₁₁ is any of Formulas 11-23 to 11-40 Displayed as one; or

A ₁₁ is represented by the formula 10-11, A ₁₂ is represented by any one of the formulas 10-22 and 10-23, L ₁₁ may be represented by any one of the formulas 11-23 to 11-40, But is not limited thereto.

According to another embodiment, A ₁₁ in the formula 1 is represented by the formula 10-11, A ₁₂ is represented by the formula 10-21, L ₁₁ is represented by the formula 11-27 to 11-34 and 11 -37 to 11-40;

A ₁₁ is represented by any one of Formulas 10-12 and 10-13, A ₁₂ is represented by any one of Formulas 10-21 to 10-23, and L ₁₁ is any of Formulas 11-23 to 11-40 Displayed as one; or

A ₁₁ is represented by the formula 10-11, A ₁₂ is represented by any one of the formulas 10-22 and 10-23, L ₁₁ is represented by any one of the formulas 11-23 to 11-40,

Of the above formulas 10-11 to 10-13, 10-21 to 10-23 and 11-23 to 11-40, R _11c , R _11f , R _12c , R _12f and R _13a to R _13f independently of one another are hydrogen A substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, A pyrimidinyl group;

An ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group substituted with deuterium; And

A phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, and a pyridyl group, which are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a hydroxyl group, a methyl group, an ethyl group, an n-propyl group, A phenyl group, a naphthyl group, a pyridinyl group, a pyrazinyl group, and a pyrimidinyl group which are substituted with at least one selected from a phenyl group, , But is not limited thereto.

Specifically, the first compound may be selected from among the following compounds E-1 to E-20, but is not limited thereto:

In the above formula (2), A ₂₁ is a group represented by any one of the following formulas (20-1) and (20-2); A ₂₂ is a group represented by the following general formula (20-1), a group represented by the following general formula (20-2), a phenyl group, a naphthyl group and a benzimidazolyl group; Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a halogen atom, A phenyl group, a naphthyl group and a benzimidazolyl group substituted with at least one member selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; Lt; / RTI &gt;

(20-1) (20-2)

In the formula, 20-1 and 20-2, X ₂₁ is a single _{bond, C [(L 27) a27} -R 26] is selected from _{[(L 28) a28 -R 27} ], O and S; X ₂₂ is _{N [(L 26) a26 -R} 25], C [(L 29) a29 -R 28] is selected from _{[(L 30) a30 -R 29} ], O and S; L ₂₂ to L ₃₀ , a ₂₂ to a ₃₀ , R ₂₁ to R _29, and b ₂₁ to b ₂₄ are described later, and * is a bonding site with neighboring atoms.

For example, in the general formulas (20-1) and (20-2), X ₂₁ is a single bond; X ₂₂ may be selected from N (R ₂₅ ), C (R ₂₈ ) (R ₂₉ ), O and S, but is not limited thereto.

In formulas (2), (20-1) and (20-2), L ₂₂ to L ₃₀ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, Substituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non-aromatic condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic groups.

For example, In the formula 2, 20-1 and 20-2, L ₂₁ to L ₃₀ are independently of each other, C ₃ -C ₁₀ cycloalkylene group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenylene group, a C ₁ -C ₁₀ heterocycloalkenylene group, a C ₆ -C ₆₀ arylene group, a divalent non-aromatic condensed polycyclic group and a divalent non-aromatic heterocyclic polycyclic group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo An alkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non- A C ₃ -C ₁₀ cycloalkylene group substituted with at least one member selected from a polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), a C ₁ -C ₁₀ heterocyclo Aromatic polycyclic group and a divalent non-aromatic heterocyclic polycyclic group such as an alkylene group, a C ₃ -C ₁₀ cycloalkenylene group, a C ₁ -C ₁₀ heterocycloalkenylene group, a C ₆ -C ₆₀ arylene group, a divalent non- ; ;

Q ₃₁ to Q ₃₃ independently represent hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups, but are not limited thereto.

As another example, in the general formulas (2), (20-1) and (20-2), L ₂₁ to L ₃₀ independently represent a phenylene group, a naphthylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, A phenylene group, a dicyclopentylene group, a dicyclopentylene group, a dicyclopentanylene group, a dicyclopentanylene group, a dicyclopentanylene group, a dicyclopentanylene group, And

Wherein R is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl, , A pyrimidinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, a phenylene group, a naphthylene group, a pyridinylene group, A thiophenylene group, a thienylene group, a thienylene group, a thienylene group, a thienylene group, a thienylene group, a thienylene group, a thienylene group, a thienylene group, , But is not limited thereto.

In the above formula (2), a21 means the number of repeating L ₂₁ , and may be selected from 0, 1, 2, 3, 4 and 5. When a21 is 0 (L _{21) a21} is a single bond, when a21 is 2 or more the plurality of L ₂₁ is the same as or different from each other.

Similarly, in the above general formulas (20-1) and (20-2), a22 to a30 are independently selected from 0, 1, 2, 3, 4 and 5.

For example, in formulas (2), (20-1), and (20-2), a21 to a30 may be independently selected from 0, 1, and 2, but are not limited thereto.

R ₂₁ to R ₂₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group , A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆ alkoxy group, a substituted or unsubstituted C ₁ -C ₆ alkoxy group, a substituted or unsubstituted C ₁ -C ₆ alkoxy group, ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Chi Or unsubstituted monovalent non-ring - is an aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 1) ( Q ₂ ) and -B (Q ₁ ) (Q ₂ ), and at least two of R ₂₁ to R ₂₉ may optionally combine to form a ring;

Q ₁ to Q ₃ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic , Biphenyl group and terphenyl group.

For one example, the general formula (2), 20-1, and 20-2, R ₂₁ to R ₂₉ are independently, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, cyano, C ₁ -C each other ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl and C ₁ -C ₁₀ heterocycloalkyl group;

Heavy hydrogen, -F, -Cl, -Br, -I, and at least one cyano group-substituted C ₁ -C ₁₀ alkyl group selected from, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl and C ₁ -C ₁₀ A heterocycloalkyl group;

C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ aryl come T, C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and Monovalent non-aromatic heterocyclic polycyclic groups;

Heavy hydrogen, -F, -Cl, -Br, -I , cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ arylthio, C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 the non-aromatic hydrocarbon ring condensed with at least one substituted C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy group selected from polycyclic group, C ₆ -C ₃₀ aryl come T, C ₁ -C ₃₀ heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And

-Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ) and -B (Q ₁ ) (Q ₂ );

Two or more of R ₂₁ to R ₂₉ may optionally combine to form a ring;

Q ₁ to Q ₃ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups, but are not limited thereto.

As another example, in the general formulas (2), (20-1) and (20-2), R ₂₁ to R ₂₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec- A butoxy group, an iso-butoxy group, a sec-butoxy group, a tert-butoxy group, a cyclopentyl group and a cyclohexyl group;

An isopropyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, an isopropyl group, a n-butyl group, , n-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, Practical skill;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, , A methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a sec-butoxy group, At least one selected from the group consisting of phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, A substituted or unsubstituted phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofurancyl group, A phenyl group; And

-Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ) and -B (Q ₁ ) (Q ₂ );

Two or more of R ₂₁ to R ₂₉ may optionally combine to form a ring;

Q ₁ to Q ₃ are each independently selected from the group consisting of hydrogen, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, , A terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; , But is not limited thereto.

In the formula 20-1, b21 is (L ₂₂₎ represents the number of ₂₁ -R _a22, is selected from 1, 2, 3 and 4. b21 is two or more when the plurality of (L _{22) a22} -R ₂₁ are the same or different from each other.

Similarly, b22 and b24 are independently selected from 1, 2, 3 and 4.

Similarly, b23 is selected from 1, 2, and 3.

According to one embodiment, in Formula 2, A ₂₁ and A ₂₂ independently of each other are represented by Formula 20-1;

A ₂₁ is represented by the above Formula 20-1, A ₂₂ is represented by the above Formula 20-2; or

A ₂₁ and A ₂₂ independently of each other may be represented by the above formula (20-2), but are not limited thereto.

According to one embodiment, the group represented by the formula (20-2) may be represented by any one of the following formulas (20-21) to (20-24), but is not limited thereto:

In the above Chemical Formulas 20-21 to 20-24, the definitions of X ₂₁ , X ₂₂ , L ₂₄ , L ₂₅ , a24, a25, R ₂₃ , R ₂₄ , b ₂₃ and b ₂₄ refer to the definition in Chemical Formula 20-2;

* Is the binding site with neighboring atoms.

According to another embodiment, the second compound may be represented by any one of the following formulas (2-1) to (2-3), but is not limited thereto:

&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

Of the above-mentioned formulas (2-1) to (2-3)

_21a X is selected from N _{[(L 21g) a21g -R 21f} ] and O, and S, X is N _22a is selected from _{[(L 22f) a22f -R 22e} ] and O, and S;

L _21a to L _21g , L _22a to L _22f and L _23a to L _23e independently of one another refer to the definition of L _{21 in} the above formula (2);

a21a to a21g, a22a to a22f and a23a to a23e independently of each other refer to the definition of a21 in Formula 2 above;

R _21a to R _21f , R _22a to R _22e, and R _23a to R _23d independently of one another refer to the definition of R ₂₁ in Formula 2;

b21b, b21e, b22a, b22c, b22d, and b23a to b23d independently of each other refer to the definition of b21 in Formula 2 above;

b21c, b21d and b22b independently of each other refer to the definition of b23 in the above formula (2).

For example, in formula (2-3), (L _23e ) _a23e may be selected from among the following formulas (9-1) to (9-6), but is not limited thereto:

Of the above formulas (9-1) to (9-6)

R ₉₁ to R ₁₀₀ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a biphenyl group, a terphenyl group, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hydrocarbon ring selected from a condensed polycyclic group, and _{-Si (Q 31) (Q 32} ) (Q 33) and;

Q ₃₁ to Q ₃₃ independently represent hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups.

For example, in Formulas (9-1) to (9-6)

R ₉₁ to R ₁₀₀ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy, phenyl, May be selected from phenyl, naphthyl, fluorenyl, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups, But is not limited thereto.

According to another embodiment, the second compound may be represented by any one of the following Formulas 2-11, 2-21 and 2-31 to 2-33, but is not limited thereto:

&Lt; Formula (2-11)

&Lt; Formula 2-21 &

&Lt; Formula 2-31 >

<Formula 2-32>

<Formula 2-33>

Of the above formulas 2-11, 2-21 and 2-31 to 2-33,

X _a , X _b and X _c are each independently selected from C and N (R _z )

X _a , X _b and X _c are not simultaneously N (R _z );

L _21a to L _21e , L _21g , L _22a to L _22f and L _23a to L _23d independently of one another refer to the definition of L ₂₁ in Formula 2 above;

a21a to a21e, a21g, a22a to a22f and a23a to a23d independently of each other refer to the definition of a21 in the above formula (2);

R _21b to R _21f , R _22a to R _22e and R _23a to R _23d independently of one another refer to the definition of R ₂₁ in Formula 2 above;

b21b, b21e, b22a, b22c, b22d, and b23a to b23d independently of each other refer to the definition of b21 in Formula 2 above;

b21c, b21d and b22b independently of one another refer to the definition of b23 in the above formula (2);

R ₉₁ to R ₁₀₀ and R _x , R _y and R _z independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, a quinolyl group, An isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

Specifically, the second compound may be selected from among the following compounds H-1 to H-19, but is not limited thereto:

For example, the third compound may emit retarded fluorescence.

According to one embodiment, the third compound may be represented by any one of the following formulas (3) and (4), but is not limited thereto:

(3)

<Formula 12-1> Formula 12-2>

&Lt; Formula 4 >

&Lt; Formula

(14-1)

Among the above-mentioned formulas 3, 4, 12-1, 12-2, 13-1 and 14-1,

R ₃₁ to R ₃₆ independently represent a group represented by the formula 12-1, a group represented by the formula 12-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, selected from substituted or unsubstituted C ₆ -C ₆₀ arylthio group and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group;

At least one of R ₃₁ to R ₃₆ is a cyano group;

At least one of R ₃₁ to R ₃₆ is selected from the group represented by the formula (12-1) and the group represented by the formula (12-2);

D ₁ is a group represented by the above formula (13-1);

A ₁ is a group represented by the above formula (14-1);

X ₄₁ is selected from a single bond, O, S, N (R ₄₇ ) and C (R ₄₇ ) (R ₄₈ );

A ₄₁ and A ₄₂ independently represent a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofurane group, A benzopyranocarbonyl group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, A benzofuran group, a benzofuranodibenzothiophen group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofurane group, and a benzothienodibenzothiophene group;

L ₄₁ and L ₄₂ are independently selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a41 and a42 are each independently selected from 0, 1, 2 and 3,

X _41a is N or C (R _41a ); X _41b is N or C (R _41b ); X _41c is N or C (R _41c ); X _41d is N or C (R _41d ); X _11e is N or C (R _41e ); At least one of X _41a to X _41e is N;

R _32a to R _32h , R ₄₁ to R ₄₈ and R _41a to R _41e independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkenyl group, alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or An unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₄ ) (Q ₅₎ and is selected from _{-B (Q 6) (Q 7} );

b45 and b46 are independently selected from 1, 2, 3, 4, 5, 6, 7 and 8;

Q ₁ to Q ₇ independently represent hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group , A C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non- An aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;

* Is the binding site with neighboring atoms.

For example, in Formula 3, one, two or three of R ₃₁ to R ₃₆ are cyano groups;

One, two, three, four or five of R ₃₁ to R ₃₆ may be selected from the group represented by the above-mentioned formula (12-1) and the group represented by the above formula (12-2) no.

As another example, in Formula 3, one or two of R ₃₁ to R ₃₆ is a cyano group;

One, two, three, four or five of R ₃₁ to R ₃₆ may be selected from the group represented by the above-mentioned formula (12-1) and the group represented by the above formula (12-2) no.

As another example, in Formula 3, one of R ₃₁ to R ₃₆ is a cyano group, and three, four or five of R ₃₁ to R ₃₆ are groups represented by Formula 12-1 and Formula 12-2; or

Two of R ₃₁ to R ₃₆ are cyano groups, and three or four of R ₃₁ to R ₃₆ may be selected from the group represented by the above formula (12-1) and the group represented by the above formula (12-2) But is not limited thereto.

For example, in Formula 3, R ₃₁ to R ₃₆ independently represent a group represented by Formula 12-1, a group represented by Formula 12-2, hydrogen, deuterium, -F, -Cl, - Br, -I, a hydroxyl group, a cyano group, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group, but is not limited thereto.

As another example, in Formula 3, R ₃₁ to R ₃₆ independently represent a group represented by Formula 12-1, a group represented by Formula 12-2, hydrogen, deuterium, -F, -Cl, - A halogen atom, a bromine atom, an iodine atom, a bromine atom, a bromine atom, a bromine atom, a bromine atom, Butoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group and tert-butoxy group.

For example, in the general formulas (12-1) and (12-2), R _32a to R _32h independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, Propyl group, isopropyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group, ethoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, tert-butoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyranyl group and pyrimidinyl group. It is not.

For example, in the above formula (13-1), A ₄₁ is a benzene group,

A ₄₂ represents a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofurane group, an indolodibenzothiophene group, An indenofluorene group, an indenofluorene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofurane group, But are not limited to, dibenzothiophene group, benzothienofluorene group, benzothienocarbazole group, benzothienodibenzofurane group and benzothienodibenzothiophene group.

For example, in Formula 13-1, X ₄₁ may be selected from a single bond and C (R ₄₇ ) (R ₄₈ ), but is not limited thereto.

According to another embodiment, the third compound may be represented by any one of the following formulas (3-1) to (3-5), but is not limited thereto:

&Lt; Formula 3-1 > < Formula 3-2 > < Formula 3-3 &

&Lt; Formula 3-4 > < Formula 3-5 &

<Formula 12-11>

Of the above-mentioned formulas (3-1) to (3-5), (12-1) and (12-2)

R _a is a group represented by the above general formula (12-11);

R ₃₃ , R ₃₄ and R ₃₆ are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group ;

R _32b and R _32g, independently of hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₃₀ together An aryl group and a C ₁ -C ₃₀ heteroaryl group,

* Is the binding site with neighboring atoms.

According to another embodiment, the third compound may be selected from among the following compounds D-1 to D-23, but is not limited thereto:

According to one embodiment, the first compound and the second compound may be different from each other, but are not limited thereto.

According to one embodiment, the second compound may satisfy the following condition 2, but is not limited thereto:

<Condition 2>

E _HOMO (C2) > -5.45 eV

Among the above conditions 2,

E _HOMO (C2) is the highest occupied molecular orbital energy level of the second compound.

Here, E _HOMO (C2) is evaluated using the DFT method of the Gaussian program which is structurally optimized at the level of B3LYP / 6-31G (d, p).

According to one embodiment, the third compound may satisfy the following condition 3, but is not limited thereto:

<Condition 3>

E _LUMO (C3) <-1.70 eV

Among the above conditions 3,

E _LUMO (C3) is the lowest unoccupied molecular orbital energy level of the third compound.

Here, E _LUMO (C3) is evaluated by DFT method of Gaussian program which is structurally optimized at B3LYP / 6-31G (d, p) level.

The composition includes the first compound represented by Formula 1, the second compound represented by Formula 2, and the third compound that satisfies Condition 1, whereby the mobility of electrons and holes can be improved. Thus, an electronic device including the composition, for example, an organic light emitting device, can have a low roll-off and a high luminous efficiency.

The first compound represented by Formula 1 necessarily includes at least one cyano group. Accordingly, the first compound represented by Formula 1 has excellent heat resistance, and an electronic device including a thin film including the first compound, the second compound, and the third compound, for example, an organic light emitting device, .

Specifically, since the composition necessarily includes the first compound represented by Formula 1, it has excellent charge mobility and material stability, and can have low roll-off and long life.

Specifically, since the composition necessarily contains the second compound represented by Formula 2, it has excellent hole mobility and material stability, and can have a relatively high efficiency and a long lifetime when mixed with the first compound.

The composition may not include a transition metal-containing organometallic compound. That is, the composition does not include a phosphorescent dopant. Therefore, the composition is clearly distinguished from other compositions in which at least one of the first to third compounds functions as a phosphorescent host.

Specifically, in the composition, the first compound and the second compound act as a host, and the third compound can act as a dopant, in particular as a delayed fluorescent dopant.

For example, HOMO, LUMO, singlet (S ₁ ), and triplet (T ₁ ) values estimated using the DFT method of the Gaussian program structurally optimized at the B3LYP / 6-31G (d, p) ) The energy level values are shown in Table 1 below.

HOMO (eV) LUMO (eV) S ₁ (eV) T ₁ (eV) Compound H-1 -4.98 -1.46 3.09 2.92 Compound H-2 -5.13 -1.09 3.61 3.15 Compound H-3 -5.42 -1.07 3.38 3.17 Compound E-1 -5.64 -2.06 3.14 3.03 Compound D-1 -5.56 -2.21 2.73 2.53 Compound D-4 -5.37 -1.93 2.81 2.63 mCBP -5.41 -1.20 3.45 3.17 DPEPO -6.31 -0.87 3.68 3.60 PO-T2T -6.92 -2.32 3.76 3.03

The weight ratio of the first compound and the second compound in the composition may be selected within the range of 0.1: 99.9 to 99.9 to 0.1, for example, 1: 9 to 9: 1. According to one embodiment, the weight ratio of the first compound to the second compound may be selected within the range of 3: 7 to 7: 3. When the composition and the weight ratio of the first compound and the second compound satisfy the ranges as described above, it is possible to achieve an effective charge balance among the light emitting layers, thereby realizing a low roll-off, high efficiency and long- have.

The content of the third compound in the composition may be selected in the range of about 0.01 to about 30% by weight based on the total weight of the first compound, the second compound and the third compound, It is not. Specifically, the content of the third compound in the composition may be selected from the range of about 5 to about 20% by weight, based on the total weight of the first compound, the second compound and the third compound, It is not. If the content of the third compound satisfies the above range, light emission without extinction phenomenon can be realized.

According to another aspect, a thin film comprising the composition is provided. The thin film may be formed by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method.

When the thin film is formed by a vacuum deposition method, the conditions for the deposition vary depending on the compound used as the thin film material, the structure and thermal properties of the desired thin film, and the like. For example, the deposition temperature is about 100 to about 500 DEG C, 10 &lt; ^-8 &gt; to about 10 &lt; ^-3 &gt; torr, and a deposition rate of about 0.01 to about 100 A / sec.

In the case of forming the thin film by spin coating, the coating conditions vary depending on the structure and thermal properties of the compound used as the thin film material and the desired thin film, but the coating speed is about 2000 rpm to about 5000 rpm, May be selected from a temperature range of about 80 DEG C to 200 DEG C, but is not limited thereto.

The thin film comprises the composition as described above.

The thin film may be applied to an organic layer of an electronic device, for example, an organic light emitting device. Thus, according to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes the composition or the thin film.

According to one embodiment, the thin film included in the organic layer may be a light emitting layer. Here, the first compound and the second compound included in the light emitting layer may serve as a host. The third compound included in the light emitting layer may serve as a dopant.

Specifically, the third compound may emit retarded fluorescence. The third compound in the light emitting layer may emit a delayed fluorescence light due to the light emitting transition of the exciton moving to the ¹ π-π * excited state from the ³ n - π * excited state through the reverse inter system crossing. The ratio of the delayed fluorescent light among the light amount emitted from the light emitting layer may be 90% or more, for example, 92% or more, and 95% or more, but is not limited thereto.

When the thin film is a light emitting layer containing the composition, the first compound and the second compound in the light emitting layer can increase the mobility of electrons and holes in the organic light emitting device and control the charge balance in the light emitting layer, , It is possible to realize an organic light emitting device having a high efficiency and a long lifetime.

On the other hand, when the thin film includes the composition, an organic light emitting device emitting blue light can be realized.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. The organic light emitting diode 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.

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

The first electrode 11 can be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. The first electrode 11 may be an anode. The first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like can be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.

The hole transporting region may be disposed between the first electrode 11 and the light emitting layer.

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

The hole transporting region may include only a hole injecting layer, or may include only a hole transporting layer. Alternatively, the hole transporting region may have a structure of a hole injecting layer / a hole transporting layer or a hole injecting layer / a hole transporting layer / an electron blocking layer which are sequentially stacked from the first electrode 11.

When the hole transporting region includes a hole injecting layer, the hole injecting layer (HIL) may be formed on the first electrode 11 by various methods such as a vacuum deposition method, a spin coating method, a casting method, an LB method, have.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, and the like. For example, 500 ° C, a degree of vacuum of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å / sec.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the structure and thermal properties of the compound used as the hole injection layer material, the desired hole injection layer, and the coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from the range of about 80 캜 to 200 캜, but is not limited thereto.

The conditions for forming the hole transporting layer and the electron blocking layer refer to conditions for forming the hole injection layer.

NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4 ', 2'- , 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate), Pani / CSA (Polyaniline / Camphor sulfonicacid (Polyaniline / camphorsulfonic acid), Pani / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 And may include at least one:

&Lt; Formula 201 >

&Lt; EMI ID =

In the above formula (201), Ar ₁₀₁ and Ar ₁₀₂ , independently of each other,

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, an acenaphthylene group, A phenylene group, a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkene group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is non-inde at least one substitution selected from the group consisting of aromatic heterocyclic condensed polycyclic group, a phenylene group, penta alkylenyl group, a carbonyl group, a naphthyl group, an azulenyl group , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a triphenylenylene group, a pyrenylene group, a phenanthrenylene group, A perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group and a perylene group;

&Lt; / RTI &gt;

In Formula 201, xa and xb may be independently an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof , phosphoric acid group or a salt thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (e.g., methoxy group, Ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group which are substituted with at least one of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

, But is not limited thereto.

In the above formula (201), R &lt; ₁₀₉ &

A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, ;

&Lt; / RTI &gt;

According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but is not limited thereto:

&Lt; Formula 201A >

In the above formula (201A), R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ are described in detail above.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, the following compounds HT1 to HT20:

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes at least one of a hole injection layer and a hole transporting layer, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å To about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

In addition to the materials described above, the hole transporting region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following compounds HT-D1 and HP-1, but the present invention is not limited thereto.

<Compound HT-D1> <F4-TCNQ>

<HP-1>

The hole transporting region may further include a buffer layer.

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

The hole transporting region may further include an electron blocking layer. The electron blocking layer may comprise a known material, for example, mCP, but is not limited thereto.

A light emitting layer (EML) may be formed on the hole transporting region by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

The light emitting layer may include a thin film as described above.

For example, the light emitting layer may have a single layer structure including only the thin film, or may have a multi-layer structure including another known light emitting layer.

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

Next, an electron transporting region is disposed above the light emitting layer.

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

For example, the electron transporting region may have a structure of a hole blocking layer / electron transporting layer / electron injecting layer or electron transporting layer / electron injecting layer, but is not limited thereto. The electron transporting layer may have a single layer or a multi-layer structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transporting layer, and the electron injecting layer in the electron transporting region will specifically be described with reference to forming conditions of the hole injecting layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, but is not limited to, at least one of the following: BCP and Bphen.

Alternatively, as the hole blocking layer material, the first compound represented by Formula 1 may be used, but the present invention is not limited thereto.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

The electron transport layer may further include at least one of the BCP, Bphen and to Alq _3, Balq, TAZ and NTAZ.

Alternatively, the electron transporting layer may include at least one of the following compounds ET1 to ET25, but is not limited thereto.

The thickness of the electron transporting layer may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transporting layer satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

The electron transporting layer may further include a metal-containing material in addition to the above-described materials.

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

The electron transport region may also include an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O and BaO.

The thickness of the electron injection layer may be from about 1 A to about 100 A, e.g., from about 3 A to about 90 A. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

A second electrode 19 is formed on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- And may be used as a material for forming the second electrode 19. Alternatively, the transmissive second electrode 19 can be formed using ITO or IZO to obtain a front light emitting element.

The organic light emitting device has been described above with reference to FIG. 1, but the present invention is not limited thereto.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, A tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the above C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, Isopropyloxy group and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure containing at least one carbon-carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, . In the present specification, the C ₂ -C ₆₀ alkenylene group means 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 at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl, propynyl propynyl), and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

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

In the present specification, a C ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the above-mentioned C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group means a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring, but does not have aromaticity , And specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, a C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, Lt; RTI ID = 0.0 &gt; a &lt; / RTI &gt; Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group means a carbamoyl group having 6 to 60 carbon atoms Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ aryl If the alkylene group contains two or more rings, the two or more rings may be fused to each other.

As used herein, a C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms , Wherein the C ₁ -C ₆₀ heteroarylene group has 2 carbons which have at least one heteroatom selected from N, O, P, Si and S as ring-forming atoms and have 1 to 60 carbocyclic aromatic systems Means a group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused together.

In the present specification, the C ₆ -C ₆₀ aryloxy group indicates -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl group), the C ₆ -C ₆₀ arylthio is -SA ₁₀₃ , And A ₁₀₃ is the above-mentioned C ₆ -C ₆₀ aryl device).

In the present specification, a monovalent non-aromatic condensed polycyclic group is a condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom (for example, the number of carbon atoms may be from 8 to 60) , And the whole molecule has a non-aromaticity. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a condensed heteropolycyclic group in which two or more rings are condensed with each other, and in addition to carbon (for example, the number of carbon atoms may be 1 to 60) Means a monovalent group comprising a heteroatom selected from N, O, P, Si and S, wherein the entire molecule has a non-aromaticity. The monovalent non-aromatic heterocyclic polycyclic group includes a carbazolyl group and the like. In the present specification, the divalent non-aromatic heterocyclic polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as a ring forming atom. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent or hexavalent group, depending on the chemical structure.

In the present specification, a C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si and S in addition to 1 to 30 carbons as a ring forming atom. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group, and may be monovalent, divalent, trivalent, tetralic, pentavalent or hexavalent, depending on the structure of the formula.

In the present specification, the substituted C ₅ -C ₃₀ carbocyclic group, the substituted C ₁ -C ₃₀ heterocyclic group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ At least one of a substituted aryl group, a heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic heterocyclic polycyclic group,

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q ₁₆₎ (Q ₁₇₎ and _{-P (= O) (Q 18} ) (Q 19) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, and A C ₁ -C ₆₀ alkoxy group;

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, 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 heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q ₂₉₎ of at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37) and _{-P (= O) (Q 38} ) (Q 39 ); &Lt; / RTI &gt;

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, " normal temperature " refers to a temperature of about 25 캜.

In the present specification, a biphenyl group is a monovalent group in which two benzenes are connected to each other through a single bond.

In the present specification, a terphenyl group is a monovalent group in which three benzenes are connected to each other through a single bond.

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

[Example]

Example 1

The glass substrate on which the ITO electrode was formed as the anode was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes each, and then subjected to UV ozone cleaning for 30 minutes.

Compound HT3 and HP-1 (concentration of HP-1 is 3% by weight) were co-deposited on the anode to form a hole injection layer having a thickness of 100 Å. Compound HT3 was deposited on the hole injection layer to form a 1350 Å thick A hole transporting layer was formed, and a hole transporting region was formed by depositing a compound H-1 on the hole transporting layer to form an electron blocking layer having a thickness of 100 Å.

Compounds E-1 and H-1 (9: 1 by weight) as a host and Compound D-1 (15% by weight based on the total weight of the host and dopant) as a dopant were co-deposited on the hole transporting region, Thick luminescent layer was formed.

Compound E-1 was vacuum-deposited on the light-emitting layer to form a hole blocking layer having a thickness of 100 Å. Compound ET17 and LiQ were co-deposited on the hole blocking layer at a weight ratio of 5: 5 to form an electron transport layer having a thickness of 300 Å Next, LiQ was deposited on the electron transporting layer to form an electron injection layer having a thickness of 10 A, and Al having a thickness of 1000 A was formed on the electron injection layer to produce an organic light emitting device.

Example  2 to 4 and Comparative Example  1 to 8

The organic light emitting device was fabricated in the same manner as in Example 1 except that the host and the dopant were changed as shown in Table 2 below.

Host Dopant The ratio of the first compound to the second compound
Weight ratio Weight ratio of dopant The first compound The second compound Third compound Example 1 E-1 H-1 D-1 9: 1 15 Example 2 E-1 H-3 D-1 9: 1 15 Example 3 E-1 H-2 D-4 7: 3 15 Example 4 E-1 H-3 D-4 9: 1 15 Comparative Example 1 DPEPO D-1 - 15 Comparative Example 2 mCBP D-1 - 40 Comparative Example 3 E-1 D-1 - 15 Comparative Example 4 H-3 PO-T2T D-1 9: 1 15 Comparative Example 5 DPEPO D-4 - 15 Comparative Example 6 mCBP D-4 - 40 Comparative Example 7 E-1 D-4 - 15 Comparative Example 8 H-3 PO-T2T D-4 9: 1 15

Evaluation Example 1: Evaluation of device characteristics

The driving voltage (at 10 cd / m ² ), the maximum external quantum efficiency (EQE _max ), the maximum power efficiency (PE _max ), the luminance of the organic light-emitting device fabricated in Examples 1 to 4 and Comparative Examples 1 to 8, (EQE, at 500 cd / m ² ), roll-off, 1- (EQE / EQE _max ), CIE color coordinates and lifetime (T ₅₀ ) characteristics were measured using a current-voltmeter (Keithley 2400) Minolta Cs-1000A). The results are summarized in Table 3. In Table _{3 T 50 (at 500 cd /} m 2) is a life data viewing time it takes the initial luminance and the luminance of 50% to 100% reference.

Host Dopant Driving voltage
(V) EQE _max
(%) PE _max
(lm / W) Luminance
(cd / m ² ) EQE
(%) Roll-off
(%) CIEx CIEy life span
(time) The first compound The second compound Third compound Example 1 E-1 H-1 D-1 3.12 19.6 51.4 500 15.8 19.4 0.20 0.36 770 Example 2 E-1 H-3 D-1 3.02 20.9 54.3 500 17.3 17.2 0.19 0.35 500 Example 3 E-1 H-2 D-4 3.16 20.7 32.6 500 20.1 2.9 0.16 0.22 225 Example 4 E-1 H-3 D-4 3.09 23.2 42.7 500 20.5 11.6 0.16 0.22 280 Comparative Example 1 DPEPO D-1 4.23 17.7 33.1 500 11.5 35.0 0.19 0.34 <1 Comparative Example 2 mCBP D-1 3.69 19.8 50.0 500 14.6 26.3 0.22 0.42 34 Comparative Example 3 E-1 D-1 2.99 19.7 46.2 500 15.0 23.9 0.19 0.33 180 Comparative Example 4 H-3 PO-T2T D-1 3.21 16.1 44.8 500 14.3 11.2 0.26 0.47 4 Comparative Example 5 DPEPO D-4 5.36 22.7 29.0 500 7.0 69.2 0.16 0.25 <1 Comparative Example 6 mCBP D-4 4.05 20.5 28.4 500 15.2 25.9 0.16 0.22 2 Comparative Example 7 E-1 D-4 3.10 22.0 39.2 500 19.6 10.9 0.16 0.22 170 Comparative Example 8 H-3 PO-T2T D-4 3.29 16.2 44.6 500 14.0 13.6 0.23 0.39 3

It can be seen from Table 3 that the organic light emitting devices fabricated in Examples 1 to 4 have higher power efficiency, higher efficiency and longer lifetime than the organic light emitting devices of Comparative Examples 1 to 8.

10: Organic light emitting device
11: first electrode
15: Organic layer
19: Second electrode

Claims (22)

A first compound represented by Formula 1 below;
A second compound represented by the following formula (2); And
And a third compound satisfying the following condition 1,
Wherein the first compound and the second compound are different from each other.
&Lt; Formula 1 >
A ₁₁ -L ₁₁ -A ₁₂
(2)
_{A 21 - (L 21) a21} -A 22
&Lt; Formula 10-1 >< EMI ID =

<Formula 11-1> Formula 11-2> Formula 11-3>

&Lt; Formula 20-1 &gt;&lt; EMI ID =

<Condition 1>
0 eV ≤ E _S1 (C3) - E _T1 (C3) ≤0.3 eV
In the above condition 1,
E _S1 (C3) is the lowest excited singlet energy level of said third compound;
E _T1 (C3) is the lowest excited triplet energy level of said third compound;
Where E _S1 (C3) and E _T1 (C3) are evaluated using a DFT method that is structurally optimized at the B3LYP / 6-31G (d, p) level;
Among the above general formulas (1) and (2)
A ₁₁ is a group represented by the above formula (10-1);
A ₁₂ is a group represented by the above formula (10-2);
L ₁₁ is a group represented by any one of formulas (11-1) to (11-3);
A ₂₁ is a group represented by any one of formulas (20-1) and (20-2);
A ₂₂ represents a group represented by the formula (20-1), a group represented by the formula (20-2), a phenyl group, a naphthyl group and a benzimidazolyl group; Or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a halogen atom, A phenyl group, a naphthyl group and a benzimidazolyl group substituted with at least one member selected from the group consisting of a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ;
X ₂₁ is a single _{bond, C [(L 27) a27} -R 26] is selected from _{[(L 28) a28 -R 27} ], O and S;
X ₂₂ is _{N [(L 26) a26 -R} 25], C [(L 29) a29 -R 28] is selected from _{[(L 30) a30 -R 29} ], O and S;
L ₂₁ to L ₃₀ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, Aromatic divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group;
a21 to a30 are each independently selected from 0, 1, 2, 3, 4 and 5;
R _11a to R _11h , R _12a to R _12h , R _13a to R _13h and R ₂₁ to R ₂₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, (CN), 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, 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, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or non-monovalent unsubstituted aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3) , -N (Q ₁ ) (Q ₂ ) and -B (Q ₁ ) (Q ₂ ), and at least two of R ₂₁ to R ₂₉ may optionally combine to form a ring;
At least one of R _11a to R _11h , R _12a to R _12h and R _13a to R _13h is a cyano group;
b21, b22 and b24 are independently of each other selected from 1, 2, 3 and 4;
b23 is selected from 1, 2 and 3;
Q ₁ to Q ₃ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic , Biphenyl group and terphenyl group;
* And * are binding sites with neighboring atoms. The method according to claim 1,
_Wherein one, two or three of R _11a to R _11h , R _12a to R _12h and R _13a to R _13h are cyano groups. The method according to claim 1,
R _11a to R _11h , R _12a to R _12h and R _13a to R _13h are each independently selected from the group consisting of hydrogen, deuterium, cyano, C ₁ -C ₁₀ alkyl and C ₁ -C ₁₀ alkoxy;
A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with at least one selected from deuterium and cyano groups;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And
Heavy hydrogen, cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, pyrazinyl group, pyrimidinyl group, carbazole group A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group which are substituted with at least one selected from a dibenzofuranyl group and a dibenzothiophenyl group; &Lt; / RTI &gt; The method according to claim 1,
A ₁₁ is represented by the following general formula (10-11), A ₁₂ is represented by the following general formula (10-21), L ₁₁ is represented by the following general formulas 11-15 to 11-22, 11-27 to 11-34, and 11-37 to 11 -40; &lt; / RTI &gt;
A ₁₁ is represented by any one of the following formulas 10-12 and 10-13, A ₁₂ is represented by any one of the following formulas 10-21 to 10-23, L ₁₁ is any one of the following formulas 11-11 to 11-40 Displayed as one; or
A ₁₁ is represented by the following formula 10-11, A ₁₂ is represented by any one of the following formulas 10-22 and 10-23, and L ₁₁ is represented by any one of the following formulas 11-11 to 11-40.

Of the above formulas 10-11 to 10-13, 10-21 to 10-23 and 11-11 to 11-40,
R _11c , R _11f , R _12c and R _12f and R _13a to R _13f are independently selected from the group consisting of hydrogen, deuterium, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, phenyl group, biphenyl group, A naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with deuterium; And
Deuterium, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, pyrazinyl group, pyrimidinyl group, carbazole group, a dibenzo A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzofuranyl group which are substituted with at least one member selected from a furanyl group and a dibenzothiophenyl group; A dibenzothiophenyl group; &Lt; / RTI &gt;
* And * are binding sites with neighboring atoms. The method according to claim 1,
Wherein said first compound is selected from the following compounds E-1 to E-20:

The method according to claim 1,
A ₂₁ and A ₂₂ independently of one another are represented by the above formula (20-1);
A ₂₁ is represented by the above Formula 20-1, A ₂₂ is represented by the above Formula 20-2; or
A ₂₁ and A ₂₂ are, independently of each other, represented by the formula (20-2). The method according to claim 1,
X ₂₁ is a single bond;
X ₂₂ is selected from N (R ₂₅ ), C (R ₂₈ ) (R ₂₉ ), O and S. The method according to claim 1,
R ₂₁ to R ₂₉ are independently of each other, hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl Alkyl group and a C ₁ -C ₁₀ heterocycloalkyl group;
Heavy hydrogen, -F, -Cl, -Br, -I, and at least one cyano group-substituted C ₁ -C ₁₀ alkyl group selected from, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl and C ₁ -C ₁₀ A heterocycloalkyl group;
C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ aryl come T, C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and Monovalent non-aromatic heterocyclic polycyclic groups;
Heavy hydrogen, -F, -Cl, -Br, -I , cyano, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy, C ₆ -C ₃₀ arylthio, C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 the non-aromatic hydrocarbon ring condensed with at least one substituted C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, C ₆ -C ₃₀ aryloxy group selected from polycyclic group, C ₆ -C ₃₀ aryl come T, C ₁ -C ₃₀ heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And
-Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₁ ) (Q ₂ ) and -B (Q ₁ ) (Q ₂ );
Two or more of R ₂₁ to R ₂₉ may optionally combine to form a ring;
Q ₁ to Q ₃ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups. The method according to claim 1,
The group represented by the formula (20-2) is represented by any one of the following formulas (20-21) to (20-24).

Of the above general formulas (20-21) to (20-24)
X ₂₁ , X ₂₂ , L ₂₄ , L ₂₅ , a24, a25, R ₂₃ , R ₂₄ , b ₂₃ and b ₂₄ refer to the definitions in the above formula (20-2);
* Is the binding site with neighboring atoms. The method according to claim 1,
Wherein the second compound is represented by any one of the following formulas (2-1) to (2-3):
&Lt; Formula (2-1)

&Lt; Formula (2-2)

<Formula 2-3>

Of the above-mentioned formulas (2-1) to (2-3)
_21a X is selected from N _{[(L 21g) a21g -R 21f} ] and O, and S, X is N _22a is selected from _{[(L 22f) a22f -R 22e} ] and O, and S;
L _21a to L _21g , L _22a to L _22f and L _23a to L _23e independently of one another refer to the definition of L _{21 in} the above formula (2);
a21a to a21g, a22a to a22f and a23a to a23e independently of each other refer to the definition of a21 in Formula 2 above;
R _21a to R _21f , R _22a to R _22e, and R _23a to R _23d independently of one another refer to the definition of R ₂₁ in Formula 2;
b21b, b21e, b22a, b22c, b22d, and b23a to b23d independently of each other refer to the definition of b21 in Formula 2 above;
b21c, b21d and b22b independently of each other refer to the definition of b23 in the above formula (2). 11. The method of claim 10,
(L _23e ) _a23e is _selected from the following formulas (9-1) to (9-6).

Of the above formulas (9-1) to (9-6)
R ₉₁ to R ₁₀₀ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, 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 heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, a biphenyl group, a terphenyl group, C ₁ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic hydrocarbon ring selected from a condensed polycyclic group, and _{-Si (Q 31) (Q 32} ) (Q 33) and;
Q ₃₁ to Q ₃₃ independently represent hydrogen, a C ₁ -C ₁₀ alkyl group, a C ₆ -C ₃₀ aryl group, a biphenyl group, a terphenyl group, a C ₁ -C ₃₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups. The method according to claim 1,
Wherein said second compound is represented by any one of the following formulas (2-11), (2-21), and (2-31) to (2-33)
&Lt; Formula (2-11)

&Lt; Formula 2-21 &

&Lt; Formula 2-31 &gt;

<Formula 2-32>

<Formula 2-33>

Of the above formulas 2-11, 2-21 and 2-31 to 2-33,
X _a , X _b and X _c are each independently selected from C and N (R _z )
X _a , X _b and X _c are not simultaneously N (R _z );
L _21a to L _21e , L _21g , L _22a to L _22f and L _23a to L _23d independently of one another refer to the definition of L ₂₁ in Formula 2 above;
a21a to a21e, a21g, a22a to a22f and a23a to a23d independently of each other refer to the definition of a21 in the above formula (2);
R _21b to R _21f , R _22a to R _22e and R _23a to R _23d independently of one another refer to the definition of R ₂₁ in Formula 2 above;
b21b, b21e, b22a, b22c, b22d, and b23a to b23d independently of each other refer to the definition of b21 in Formula 2 above;
b21c, b21d and b22b independently of one another refer to the definition of b23 in the above formula (2);
R ₉₁ to R ₁₀₀ and R _x , R _y and R _z independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, a quinolyl group, An isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. The method according to claim 1,
Wherein said second compound is selected from the following compounds H-1 to H-19:

The method according to claim 1,
Wherein the third compound releases retarded fluorescence. The method according to claim 1,
Wherein the third compound is represented by any one of the following formulas (3) and (4):
(3)

<Formula 12-1> Formula 12-2>

&Lt; Formula 4 &gt;

&Lt; Formula

(14-1)

Among the above-mentioned formulas 3, 4, 12-1, 12-2, 13-1 and 14-1,
R ₃₁ to R ₃₆ independently represent a group represented by the formula 12-1, a group represented by the formula 12-2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, selected from substituted or unsubstituted C ₆ -C ₆₀ arylthio group and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group;
At least one of R ₃₁ to R ₃₆ is a cyano group;
At least one of R ₃₁ to R ₃₆ is selected from the group represented by the formula (12-1) and the group represented by the formula (12-2);
D ₁ is a group represented by the above formula (13-1);
A ₁ is a group represented by the above formula (14-1);
X ₄₁ is selected from a single bond, O, S, N (R ₄₇ ) and C (R ₄₇ ) (R ₄₈ );
A ₄₁ and A ₄₂ independently represent a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofurane group, A benzopyranocarbonyl group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, A benzofuran group, a benzofuranodibenzothiophen group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofurane group, and a benzothienodibenzothiophene group;
L ₄₁ and L ₄₂ are independently selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a41 and a42 are each independently selected from 0, 1, 2 and 3,
X _41a is N or C (R _41a ); X _41b is N or C (R _41b ); X _41c is N or C (R _41c ); X _41d is N or C (R _41d ); X _11e is N or C (R _41e ); At least one of X _41a to X _41e is N;
R _32a to R _32h , R ₄₁ to R ₄₈ and R _41a to R _41e independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkenyl group, alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or An unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), -N (Q ₄ ) (Q ₅₎ and is selected from _{-B (Q 6) (Q 7} );
b45 and b46 are independently selected from 1, 2, 3, 4, 5, 6, 7 and 8;
Q ₁ to Q ₇ independently represent hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group , A C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non- An aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
* Is the binding site with neighboring atoms. 16. The method of claim 15,
One, two or three of R ₃₁ to R ₃₆ is a cyano group;
1, 2, 3, 4 or 5 of R ₃₁ to R ₃₆ are selected from the group represented by the formula (12-1) and the group represented by the formula (12-2). The method according to claim 1,
Wherein the third compound is represented by any one of the following formulas (3-1) to (3-5):
&Lt; Formula 3-1 >< Formula 3-2 >< Formula 3-3 &

&Lt; Formula 3-4 >< Formula 3-5 &

<Formula 12-11>

Of the above-mentioned formulas (3-1) to (3-5), (12-1) and (12-2)
R _a is a group represented by the above general formula (12-11);
R ₃₃ , R ₃₄ and R ₃₆ are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group ;
R _32b and R _32g, independently of hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₃₀ together An aryl group and a C ₁ -C ₃₀ heteroaryl group,
* Is the binding site with neighboring atoms. The method according to claim 1,
Wherein said third compound is selected from the following compounds D-1 to D-23:

The method according to claim 1,
Wherein the transition metal-containing organometallic compound is free of transition metal-containing organometallic compounds. A thin film comprising the composition of any one of claims 1 to 19. A first electrode; A second electrode; And
And an organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises the thin film of claim 20. 22. The method of claim 21,
Wherein the thin film is a light emitting layer.

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