Heterocyclic compound, organic light-emitting element comprising same, and electronic device

Abstract

Disclosed are a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting element including the same, and an electronic device including the organic light-emitting element: lt; chemical formula 1gt; in the chemical formula 1, the description of each substituent group refers to the specification.

Description

Technical Field

[0001] The invention relates to a heterocyclic compound, an organic light-emitting element comprising the heterocyclic compound, and an electronic device. Background Art

[0002] Among light-emitting elements, self-luminous elements not only have a wide viewing angle and excellent contrast, but also have a short response time and excellent brightness, driving voltage and response speed characteristics.

[0003] The light-emitting element may have a structure in which a first electrode is arranged on the upper part of a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are arranged in sequence on the upper part of the first electrode. Holes injected from the first electrode move to the light-emitting layer via the hole transport region, and electrons injected from the second electrode move to the light-emitting layer via the electron transport region. Carriers such as the holes and the electrons recombine in the light-emitting layer region to generate excitons. The excitons generate light while changing from an excited state to a ground state. Summary of the invention

[0004] Provided are a novel heterocyclic compound, an organic light-emitting element comprising the same, and an electronic device.

[0005] According to one aspect, a heterocyclic compound is provided, represented by the following Chemical Formula 1:

[0006] <Chemical Formula 1>

[0007]

[0008] <Chemical Formula 2>

[0009]

[0010] <Chemical formula 3>

[0011]

[0012] In the chemical formula 1, the chemical formula 2 and the chemical formula 3,

[0013] Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 ,Ar 31 ,Ar 32 ,Ar41 and Ar 42 Independently of each other, C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0014] T 1 、T 2 、T 3 and T 4 Independently of each other, N(Y 2 )、N(Y 3 )、N(R 6 )、P(R 6 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 ), O, S or Se,

[0015] Y 2 is a group represented by the chemical formula 2,

[0016] Y 3 is a group represented by the chemical formula 3,

[0017] a1 and a2 are independently 0, 1 or 2,

[0018] The sum of a1 and a2 is greater than 1,

[0019] T 41 is O or S,

[0020] * is the binding site with the adjacent nitrogen atom,

[0021] X 3 , X 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Z 1 , Z 2 , Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z 4 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazo, and are 10a Substituted or unsubstituted C 1 -C60 Alkyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkenyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Aryl, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Arylthio, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroaryl, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroaryloxy, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroarylthio, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a Substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2)、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0022] X 3 , X 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z 1 , Z 2 , Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z 4 Two or more adjacent ones of the R can be optionally combined with each other to form a 10a Substituted or unsubstituted C 5 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0023] n1, n2, n3, n4 and n5 are each independently an integer from 0 to 10,

[0024] m1, m2, m31, m32 and m4 are independently integers from 0 to 15,

[0025] The R 10a for,

[0026] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0027] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy;

[0028] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group, C 1 -C 60Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 arylthio; or

[0029] Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )

[0030] Or P(=O)(Q 31 )(Q 32 ),

[0031] The Q 1 To the Q 3 Q 11 To the Q 13 Q 21 To the Q 23 And the Q 31 To the Q 33 independently of each other are hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or deuterated, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0032] According to another aspect, an organic light-emitting element is provided, comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer comprising a light-emitting layer sandwiched between the first electrode and the second electrode, wherein the organic light-emitting element comprises more than one heterocyclic compound.

[0033] According to another aspect, an electronic device including the organic light emitting element is provided.

[0034] According to another aspect, a consumer product including the organic light emitting element is provided.

[0035] The organic light emitting element including the heterocyclic compound can have high color purity, high efficiency and long life. In addition, the organic light emitting element can be used to manufacture high-quality electronic devices and consumer products. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 is a diagram schematically showing the structure of an organic light emitting element according to an implementation example.

[0037] Figure 2 is a diagram schematically showing the structure of a light emitting device according to an implementation example.

[0038] Figure 3 is a diagram schematically showing the structure of a light emitting device according to another implementation example.

[0039] Figure 4 is a perspective view schematically showing an electronic device including an organic light emitting element according to an implementation example.

[0040] Figure 5 FIG. 1 is a diagram schematically showing the exterior of a vehicle as an electronic device including an organic light emitting element according to an implementation example of the present invention.

[0041] Figures 6a to 6c 2 is a diagram schematically showing the interior of a vehicle according to various implementation examples of the present invention.

[0042] Description of Reference Numerals

[0043] 10: Organic light emitting element 110: First electrode

[0044] 130: Intermediate layer 150: Second electrode DETAILED DESCRIPTION

[0045] According to one aspect of the present invention, a heterocyclic compound is provided.

[0046] The heterocyclic compound is represented by the following chemical formula 1:

[0047] <Chemical Formula 1>

[0048]

[0049] <Chemical Formula 2>

[0050]

[0051] <Chemical formula 3>

[0052]

[0053] In the chemical formula 1, T 1 、T 2 、T 3 and T 4 can be independently N(Y 2 )、N(Y 3 )、N(R 6 )、P(R 6 )、C(R 7 )(R 8 )、Si(R 7 )(R 8 ), O, S or Se. Among them, Y 2 is a group represented by the chemical formula 2, Y 3 is a group represented by the chemical formula 3.

[0054] According to an implementation example, T 1 、T 2 、T 3 and T 4 can be independently N(Y 2 )、N(Y 3 )、N(R 6 ), O, S or Se.

[0055] According to an implementation example, T 1 、T 2 、T 3 and T 4 At least one of them can be N(Y 2 ).

[0056] According to an implementation example, T 1 、T 2 、T 3 and T 4 At least one of them can be N(Y 3 ).

[0057] In the chemical formula 1, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 Independently of each other, C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0058] According to an implementation example, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 ,Ar 5 ,Ar 11 ,Ar 12 ,Ar 21 and Ar 22 may be independently a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, indene group, fluorene group, spirobifluorene group, benzofluorene group, dibenzofluorene group, indole group, pyridine group, pyrimidine group, carbazole group, benzocarbazole group, dibenzocarbazole group, furan group, benzofuran group, dibenzofuran group, naphthofuran group, benzonaphthofuran group, dinaphthofuran group, thiophene group, benzothiophene group, dibenzothiophene group, naphthiophene group, benzonaphthothiophene group or dinaphthothiophene group.

[0059] According to an implementation example, the heterocyclic compound represented by the chemical formula 1 may be a compound represented by the following chemical formula 1-1:

[0060] <Chemical Formula 1-1>

[0061]

[0062] In the chemical formula 1-1,

[0063] For Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 、T 1 、T 2 、T 3 、T 4 , a1, a2, X 3 , X 4 , R 1 , R 2 , Z 1 , Z 2 , n1, n2, m1 and m2, refer to the contents described in this manual,

[0064] For R 31 and R 32 The description of R in this specification is independent of each other. 3 Description,

[0065] For R 41 and R 42The description of R in this specification is independent of each other. 4 Description,

[0066] For R 51 and R 52 The description of R in this specification is independent of each other. 5 Description.

[0067] According to an implementation example, the The group represented by may be a group represented by the following chemical formula 1A, wherein The group represented by may be a group represented by the following Chemical Formula 1B:

[0068] <Chemical Formula 1A>

[0069]

[0070] <Chemical Formula 1B>

[0071]

[0072] In the chemical formula 1A and the chemical formula 1B,

[0073] For Z 11 To Z 18 The description of Z in this specification is independent of each other. 1 Description,

[0074] For Z 21 To Z 28 The description of Z in this specification is independent of each other. 2 Description,

[0075] *' is the binding site with the adjacent atom.

[0076] In the chemical formula 1, a1 and a2 may be 0, 1 or 2 independently of each other, and the sum of a1 and a2 may be 1 or more.

[0077] According to an implementation example, any one of the following conditions i) to iii) may be satisfied.

[0078] i) a1 is 1, a2 is 0;

[0079] ii) a1 is 0 and a2 is 1; or

[0080] iii) a1 and a2 are both 1.

[0081] According to an implementation example, the heterocyclic compound represented by the chemical formula 1 may be a compound represented by any one of the following chemical formulas 1-21 to 1-23:

[0082] <Chemical Formula 1-21>

[0083]

[0084] <Chemical Formula 1-22>

[0085]

[0086] <Chemical Formula 1-23>

[0087]

[0088] In the chemical formula 1-21, the chemical formula 1-22 and the chemical formula 1-23,

[0089] For Ar 3 ,Ar 4 ,Ar 5 ,Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 、T 1 、T 2 、T 3 、T 4 , X 3 , X 4 , R 3 , R 4 , R 5 , Z 1 , Z 2 For the descriptions of n3, n4, n5, m1 and m2, refer to the contents described in this manual.

[0090] For R 11 , R 12 , R 13 , R 14 The description of R in this specification is independent of each other. 1 Description,

[0091] For R 21 , R 22 , R 23 and R 24 The description of R in this specification is independent of each other. 2 Description.

[0092] In the chemical formula 1, Y 2 It is a group represented by the following Chemical Formula 2.

[0093] <Chemical Formula 2>

[0094]

[0095] In the chemical formula 2, Ar 31 and Ar 32 Can be independently C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0096] According to an implementation example, Ar 31 and Ar 32 may be independently a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, indene group, fluorene group, spirobifluorene group, benzofluorene group, dibenzofluorene group, indole group, pyridine group, pyrimidine group, carbazole group, benzocarbazole group, dibenzocarbazole group, furan group, benzofuran group, dibenzofuran group, naphthofuran group, benzonaphthofuran group, dinaphthofuran group, thiophene group, benzothiophene group, dibenzothiophene group, naphthiophene group, benzonaphthothiophene group or dinaphthothiophene group.

[0097] According to an implementation example, the group represented by the chemical formula 2 may be a group represented by the following chemical formula 2-1:

[0098] <Chemical Formula 2-1>

[0099]

[0100] In the chemical formula 2-1,

[0101] For Z 3A To Z 3C Please refer to the contents of this manual for instructions.

[0102] For Z 3D To Z 3H The description of Z in this specification is independent of each other. 31 Description,

[0103] For Z 3I To Z 3M The description of Z in this specification is independent of each other. 32 Description.

[0104] In the chemical formula 2 and the chemical formula 2-1, * represents a bonding site with an adjacent nitrogen atom.

[0105] In the chemical formula 1, Y 3 It is a group represented by the following Chemical Formula 3.

[0106] <Chemical formula 3>

[0107]

[0108] In the chemical formula 3, T 41 Can be O or S.

[0109] In the chemical formula 3, Ar 41 and Ar 42 Can be independently C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0110] According to an implementation example, Ar 41 and Ar 42 may be independently a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, indene group, fluorene group, spirobifluorene group, benzofluorene group, dibenzofluorene group, indole group, pyridine group, pyrimidine group, carbazole group, benzocarbazole group, dibenzocarbazole group, furan group, benzofuran group, dibenzofuran group, naphthofuran group, benzonaphthofuran group, dinaphthofuran group, thiophene group, benzothiophene group, dibenzothiophene group, naphthiophene group, benzonaphthothiophene group or dinaphthothiophene group.

[0111] According to an implementation example, the group represented by the chemical formula 3 may be a group represented by any one of the following chemical formulas 3-1 to 3-4:

[0112] <Chemical Formula 3-1>

[0113]

[0114] <Chemical Formula 3-2>

[0115]

[0116] <Chemical Formula 3-3>

[0117]

[0118] <Chemical Formula 3-4>

[0119]

[0120] In the chemical formula 3-1 to the chemical formula 3-4,

[0121] For T 41 Please refer to the contents of this manual for instructions.

[0122] For Z41 To Z 48 The description of Z in this specification is independent of each other. 4 Description.

[0123] According to a preferred implementation example, the group represented by the chemical formula 3 may be the group represented by the chemical formula 3-1.

[0124] In the chemical formula 3 and the chemical formula 3-1 to the chemical formula 3-4, * is a bonding site with an adjacent nitrogen atom.

[0125] In the chemical formula 1, the chemical formula 2 and the chemical formula 3, X 3 , X 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Z 1 , Z 2 , Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z 4 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazo, and at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkenyl, with at least one R 10aSubstituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Aryl, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Arylthio, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroaryl, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroaryloxy, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroarylthio, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a Substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ).

[0126] Among them, X 3 , X 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z 1 , Z 2 , Z3A , Z 3B , Z 3C , Z 31 , Z 32 and Z 4 Two or more adjacent ones of the R can be optionally combined with each other to form a 10a Substituted or unsubstituted C 5 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0127] According to an implementation example, the R 6 can be at least one R 10a Substituted or unsubstituted C 6 -C 20 Aryl or at least one R 10a Substituted or unsubstituted C 1 -C 20 Heteroaryl.

[0128] According to an implementation example, the X 3 And the X 4 can be independently hydrogen, deuterium, hydroxyl, 10a Substituted or unsubstituted C 1 -C 10 Alkyl, with at least one R 10a Substituted or unsubstituted C 2 -C 10 Alkenyl, with at least one R 10a Substituted or unsubstituted C 2 -C 10 Alkynyl, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkenyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C 6 -C 20 Aryl, with at least one R 10aSubstituted or unsubstituted C 1 -C 20 Heteroaryl, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a Substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 ) or P(Q 1 )(Q 2 ).

[0129] In the Chemical Formulas 1, 2 and 3, n1, n2, n3, n4 and n5 may be integers of 0 to 10 independently of one another, and m1, m2, m31, m32 and m4 may be integers of 0 to 15 independently of one another.

[0130] In the chemical formulas 1, 2 and 3,

[0131] The R 10a Can be,

[0132] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0133] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60Alkynyl or C 1 -C 60 Alkoxy;

[0134] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 arylthio; or

[0135] Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )

[0136] Or P(=O)(Q 31 )(Q 32 ),

[0137] The Q 1 To the Q 3 Q 11 To the Q 13 Q 21 To the Q 23 And the Q 31 To the Q 33 can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or deuterated, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0138] According to an implementation example, the heterocyclic compound represented by the chemical formula 1 may be one of the following compounds 1 to 80, but is not limited thereto:

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] The heterocyclic compound represented by the chemical formula 1 satisfies the following conditions: At least one substituent is introduced into the ring Ar of the heterocyclic ring including two boron atoms 1 or Ar 2 By using such a structure, the heterocyclic compound can have a lower highest occupied molecular orbital energy (E HOMO ) and a smaller ΔE S-T(the difference between triplet energy and singlet energy), according to the reverse intersystem crossing (RISC) mechanism, the speed of conversion of triplet excitons to singlet excitons can be increased. In addition, the heterocyclic compound can exhibit high color purity.

[0146] Therefore, when the heterocyclic compound represented by the chemical formula 1 is applied to an organic light-emitting element, the efficiency and life characteristics of the element can be significantly improved. For example, by including the heterocyclic compound represented by the chemical formula 1 in the light-emitting layer, a deep blue organic light-emitting element with high color purity, high efficiency and long life can be realized.

[0147] While not being bound by a particular theory, ΔE S-T The value is reduced by having a core including two boron atoms, and accordingly, the speed at which triplet excitons are converted into singlet excitons can be increased according to the RISC mechanism. Therefore, an organic light emitting element using the heterocyclic compound represented by the Chemical Formula 1 can improve efficiency.

[0148] While not being bound by a particular theory, the introduction of 1 or cyclic Ar 2 The 9-carbazole plays a role in protecting the active site of the distributed core orbital, thereby inhibiting the formation of polarons based on intermolecular interactions and inhibiting triplet exciton dexter energy transfer. 1 or cyclic Ar 2 The 9-carbazole in the HOMO ), thereby suppressing the trap effect of the dopant. Therefore, the organic light emitting element using the heterocyclic compound represented by the chemical formula 1 can improve the life span.

[0149] Although not limited to a particular theory, 9-carbazole is introduced into the ring Ar in a para-orientation with respect to the boron atom. 1 or cyclic Ar 2 , thereby strengthening the multiple resonance effect and increasing the speed of converting triplet excitons to singlet excitons according to the RISC mechanism. Therefore, the organic light emitting element using the heterocyclic compound represented by the chemical formula 1 can improve efficiency.

[0150] The heterocyclic compound may emit blue light. For example, the heterocyclic compound may emit blue light having a maximum emission wavelength of 400 nm or more and less than 500 nm (e.g., a maximum emission wavelength of 410 nm or more and less than 490 nm) (back emission CIE x,y The color coordinates are 0.15, 0.05 to 0.15), but are not limited thereto. Thus, the heterocyclic compound represented by the chemical formula 1 can be usefully used in the manufacture of an organic light emitting element that emits blue light.

[0151] According to an implementation example, the heterocyclic compound can emit deep blue light having a maximum emission wavelength of 410 nm to 465 nm. For example, the heterocyclic compound can emit deep blue light having a maximum emission wavelength of 410 nm to 460 nm.

[0152] The synthesis method of the heterocyclic compound represented by the chemical formula 1 can be understood by those skilled in the art with reference to the examples described below.

[0153] According to another aspect, an organic light-emitting element is provided, comprising: a first electrode; a second electrode; an intermediate layer including a light-emitting layer sandwiched between the first electrode and the second electrode, and the organic light-emitting element comprises more than one heterocyclic compound.

[0154] According to an implementation example,

[0155] The first electrode of the organic light emitting element is an anode,

[0156] The second electrode of the organic light emitting element is a cathode,

[0157] The intermediate layer further includes a hole transport region arranged between the first electrode and the light emitting layer and an electron transport region arranged between the light emitting layer and the second electrode,

[0158] The hole transport region includes a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, an electron blocking layer or any combination thereof,

[0159] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0160] According to an implementation example, the electron transport region may include a hole blocking layer.

[0161] According to an implementation example, the hole blocking layer may be in direct contact with the light emitting layer.

[0162] According to an implementation example, the hole blocking layer may include a compound containing phosphine oxide, a compound containing a silyl group, or a combination thereof.

[0163] According to another implementation example, the light emitting layer may include the heterocyclic compound represented by the Chemical Formula 1. For example, the light emitting layer may emit blue light having a maximum light emission wavelength of 400 nm to 500 nm.

[0164] According to another implementation example, the light-emitting layer of the organic light-emitting element includes a dopant and a host, and the heterocyclic compound represented by the chemical formula 1 may be included in the dopant. That is, the heterocyclic compound may play the role of a dopant. The light-emitting layer may emit blue light, for example. The blue light may have a maximum emission wavelength in the range of 400 nm to 500 nm, for example.

[0165] According to an implementation example, the light emitting layer can emit deep blue light having a maximum light emission wavelength of 410 nm to 465 nm. For example, the light emitting layer can emit deep blue light having a maximum light emission wavelength of 410 nm to 460 nm.

[0166] According to an implementation example, the light-emitting layer may include a host and a dopant.

[0167] According to an implementation example, the light-emitting layer may further include a photosensitizer.

[0168] According to an implementation example, in the light-emitting layer, the content of the host may be greater than the content of the dopant based on weight.

[0169] According to an implementation example, the main body may include a silicon-containing compound, a phosphine oxide-containing compound, or a combination thereof.

[0170] According to an implementation example, the subject may refer to the description of the subject recorded in this specification.

[0171] Therefore, the organic light emitting element including the heterocyclic compound represented by Chemical Formula 1 as described above may have high color purity, high efficiency, and long life characteristics.

[0172] According to an implementation example, the heterocyclic compound represented by the chemical formula 1 can emit blue light. For example, the heterocyclic compound represented by the chemical formula 1 can emit blue light having a maximum emission wavelength in the range of 390nm to 500nm, 410nm to 500nm, 410nm to 490nm, 430nm to 480nm, 440nm to 475nm, or 455nm to 470nm.

[0173] According to another implementation example, the heterocyclic compound represented by the chemical formula 1 may have a back-emitting CIEx Coordinates in the range of 0.12 to 0.15 or 0.13 to 0.14 and back-illuminated CIE y Color purity with coordinates ranging from 0.06 to 0.25, 0.10 to 0.20, or 0.13 to 0.20.

[0174] In this specification, the term "intermediate layer" refers to all layers of a single layer and / or a plurality of layers disposed between the first electrode and the second electrode in the organic light emitting element.

[0175] According to another aspect, an electronic device including the organic light-emitting element as described above is provided. The electronic device may also include a thin film transistor. For example, the electronic device may also include a thin film transistor including a source electrode and a drain electrode, and the first electrode of the organic light-emitting element may be electrically connected to the source electrode or the drain electrode. In addition, the electronic device may also include a color filter, a color conversion layer, a touch screen layer, a polarization layer or any combination thereof. For a more detailed description of the electronic device, refer to the contents described in this specification.

[0176] According to yet another aspect, there is provided a consumer product comprising the organic light emitting element as described above.

[0177] For example, the electronic consumer product can be a flat panel display, a curved display, a computer monitor, a medical display, a television, a billboard, indoor or outdoor lighting and / or signaling, a head-up display, a fully transparent or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a portable phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a notebook computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device or a sign.

[0178] [right Figure 1 Description]

[0179] Figure 1 1 is a cross-sectional view schematically showing an organic light emitting element 10 according to an embodiment of the present invention. The organic light emitting element 10 includes a first electrode 110 , an intermediate layer 130 and a second electrode 150 .

[0180] Below, we will refer to Figure 1 The structure and manufacturing method of the organic light emitting element 10 according to an embodiment of the present invention are described as follows.

[0181] [First electrode 110]

[0182] The substrate may be additionally arranged on Figure 1 The lower part of the first electrode 110 or the upper part of the second electrode 150 is formed by a conductive layer. As the substrate, a glass substrate or a plastic substrate can be used. Alternatively, the substrate can be a flexible substrate, for example, a plastic having excellent heat resistance and durability such as polyimide, polyethylene terephthalate (PET: polyethylene terephthalate), polycarbonate (polycarbonate), polyethylene naphthalate (polyethylene naphthalate), polyarylate (PAR: polyarylate), polyetherimide (polyetherimide) or any combination thereof.

[0183] The first electrode 110 can be formed, for example, by providing a first electrode material on the substrate by deposition or sputtering. When the first electrode 110 is an anode, a high work function material that can easily inject holes can be used as the first electrode material.

[0184] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode or a transmissive electrode. In order to form the first electrode 110 as a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) or any combination thereof as the first electrode material. Alternatively, in order to form the first electrode 110 as a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof can be used as the first electrode material.

[0185] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0186] [Middle layer 130]

[0187] An intermediate layer 130 is disposed on the first electrode 110. The intermediate layer 130 includes a light emitting layer.

[0188] The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the light emitting layer and an electron transport region disposed between the light emitting layer and the second electrode 150 .

[0189] The intermediate layer 130 may include metal-containing compounds such as heterocyclic compounds, inorganic substances such as quantum dots, etc., in addition to various organic substances.

[0190] In addition, the intermediate layer 130 may include: i) two or more emitting units, sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer, arranged between the two emitting units. In the case where the intermediate layer 130 includes the emitting units and the charge generation layer as described above, the organic light emitting element 10 may be a tandem organic light emitting element.

[0191] [Hole Transport Region in Intermediate Layer 130]

[0192] The hole transport region may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing a plurality of substances different from each other; or iii) a multi-layer structure including a plurality of layers containing a plurality of substances different from each other.

[0193] The hole transport region may include a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer or any combination thereof.

[0194] For example, the hole transport region may have a multilayer structure of hole injection layer / hole transport layer, hole injection layer / hole transport layer / luminescence auxiliary layer, hole injection layer / luminescence auxiliary layer, hole transport layer / luminescence auxiliary layer or hole injection layer / hole transport layer / electron blocking layer stacked in sequence starting from the first electrode 110.

[0195] The hole transport region may include a compound represented by the following Chemical Formula 201, a compound represented by the following Chemical Formula 202, or any combination thereof:

[0196] <Chemical Formula 201>

[0197]

[0198] <Chemical formula 202>

[0199]

[0200] In the chemical formula 201 and the chemical formula 202,

[0201] L 201 To L 204 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0202] L 205 For *-O-*', *-S-*', *-N(Q 201 )-*', by at least one R 10a Substituted or unsubstituted C 1 -C 20 Alkylene, with at least one R 10a Substituted or unsubstituted C 2 -C 20 Alkenylene, with at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0203] xa1 to xa4 are independently one of integers from 0 to 5,

[0204] xa5 is an integer from 1 to 10,

[0205] R 201 To R 204 and Q 201 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0206] R 201 and R 202 can be optionally connected via a single bond, by at least one R 10aSubstituted or unsubstituted C 1 -C 5 Alkylene or at least one R 10a Substituted or unsubstituted C 2 -C 5 Alkenylene groups are connected to each other to form a 10a Substituted or unsubstituted C 8 -C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., refer to the following compound HT16, etc.),

[0207] R 203 and R 204 can be optionally connected via a single bond, by at least one R 10a Substituted or unsubstituted C 1 -C 5 Alkylene or at least one R 10a Substituted or unsubstituted C 2 -C 5 Alkenylene groups are connected to each other to form a 10a Substituted or unsubstituted C 8 -C 60 polycyclic groups, and

[0208] na1 can be one of integers from 1 to 4.

[0209] For example, the chemical formula 201 and the chemical formula 202 may respectively include at least one of the groups represented by the following chemical formulas CY201 to CY217:

[0210]

[0211] In the chemical formula CY201 to the chemical formula CY217, R 10b and R 10c For the description of R 10a Description, and ring CY 201 To Ring CY 204 Can be independently C 3 -C 20 Carbocyclic group or C 1 -C 20 heterocyclic group, at least one hydrogen in the chemical formula CY201 to the chemical formula CY217 may be replaced by R as described in the specification 10a Replaced or not replaced.

[0212] According to an implementation example, the ring CY in the chemical formula CY201 to the chemical formula CY217 201 To Ring CY204 They may be independently a benzene group, a naphthalene group, a phenanthrene group or an anthracene group.

[0213] According to another embodiment, the chemical formula 201 and the chemical formula 202 may respectively include at least one of the groups represented by the chemical formulas CY201 to CY203.

[0214] According to still another embodiment, the chemical formula 201 may include at least one of the groups represented by the chemical formulas CY201 to CY203 and at least one of the groups represented by the chemical formulas CY204 to CY217, respectively.

[0215] According to another implementation example, in the chemical formula 201, xa1 may be 1, R 201 may be a group represented by one of the chemical formulas CY201 to CY203, xa2 may be 0, R 202 It may be a group represented by one of the chemical formulas CY204 to CY207.

[0216] According to yet another implementation example, each of the chemical formula 201 and the chemical formula 202 may not include the groups represented by the chemical formulas CY201 to CY203.

[0217] According to yet another implementation example, each of the chemical formula 201 and the chemical formula 202 may not include the groups represented by the chemical formulas CY201 to CY203, but may include at least one of the groups represented by the chemical formulas CY204 to CY217.

[0218] As yet another example, each of the chemical formula 201 and the chemical formula 202 may not include the groups represented by the chemical formulas CY201 to CY217.

[0219] For example, the hole transport region may include one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA: 4,4',4"-tris(N-carbazolyl)triphenylamine), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA: Polyaniline / Dodecylbenzenesulfonic acid), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS: Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), polyaniline / camphorsulfonic acid (PANI / CSA: Polyaniline / Camphor sulfonic acid acid), polyaniline / poly(4-styrenesulfonate) (PANI / PSS: Polyaniline / Poly(4-styrenesulfonate)) or any combination thereof:

[0220]

[0221]

[0222]

[0223]

[0224]

[0225] The thickness of the hole transport region may be about to about (For example, about to about ). In the case where the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about (For example, about to about ), the thickness of the hole transport layer may be about to about (For example, about to about ). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the aforementioned ranges, satisfactory hole transport characteristics can be obtained without substantially increasing the driving voltage.

[0226] The light-emitting auxiliary layer is a layer that increases the light emission efficiency by compensating for the optical resonance distance caused by the wavelength of light emitted from the light-emitting layer, and the electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport region. The above-mentioned substances that can be included in the hole transport region can be included in the light-emitting auxiliary layer and the electron blocking layer.

[0227] [p-dopant]

[0228] In addition to the above-mentioned substances, the hole transport region may include a charge generating substance for improving conductivity. The charge generating substance may be uniformly or non-uniformly dispersed (eg, in the form of a single layer consisting of the charge generating substance) in the hole transport region.

[0229] The charge generating substance may be, for example, a p-dopant.

[0230] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.

[0231] According to an implementation example, the p-dopant may include a quinone derivative, a cyanide-containing compound, a compound containing the element EL1 and the element EL2, or any combination thereof.

[0232] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.

[0233] Examples of the cyano group-containing compound may include HAT-CN, a compound represented by the following Chemical Formula 221, and the like.

[0234]

[0235] <Chemical Formula 221>

[0236]

[0237] In the chemical formula 221,

[0238] R 221 To R 223 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C1 -C 60 Heterocyclic groups,

[0239] The R 221 To R 223 At least one of them may be independently C substituted by the following groups 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group: cyano; -F; -Cl; -Br; -I; C substituted by cyano, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 or any combination thereof.

[0240] In the compound containing the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid or a combination thereof, and the element EL2 may be a non-metal, a metalloid or a combination thereof.

[0241] Examples of the metal may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc.); (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.), etc.

[0242] Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.

[0243] Examples of the non-metal may include oxygen (O), halogen (eg, F, Cl, Br, I, etc.), and the like.

[0244] For example, the compound containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0245] Examples of the metal oxide may include tungsten oxide (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.), rhenium oxides (e.g., ReO 3 etc.

[0246] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.

[0247] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.

[0248] Examples of the alkaline earth metal halide may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI2 MgI 2 ,CaI 2 , SrI 2 ,BaI 2 wait.

[0249] Examples of the transition metal halide may include titanium halide (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.

[0250] Examples of the late transition metal halide may include zinc halides (eg, ZnF 2 、ZnCl 2 、ZnBr2 、ZnI 2 etc.), indium halides (e.g., InI 3 etc.), tin halides (e.g., SnI 2 etc.

[0251] Examples of the lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 、SmI 3 wait.

[0252] Examples of the metalloid halide may include antimony halides (eg, SbCl 5 etc.

[0253] Examples of the metal telluride may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.

[0254] [Light Emitting Layer in Intermediate Layer 130]

[0255] In the case where the organic light emitting element 10 is a full-color organic light emitting element, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer and / or a blue light emitting layer according to independent sub-pixels. Alternatively, the light emitting layer may have a structure in which two or more layers of the red light emitting layer, the green light emitting layer and the blue light emitting layer are stacked in a contact or spaced manner, or have a structure in which two or more substances of the red light emitting substance, the green light emitting substance and the blue light emitting substance are mixed without distinguishing between layers, thereby emitting white light.

[0256] The light emitting layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant or any combination thereof.

[0257] The dopant in the light emitting layer may be included in an amount of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.

[0258] Furthermore, the light emitting layer may include quantum dots.

[0259] In addition, the light emitting layer may include a delayed fluorescent substance. The delayed fluorescent substance may function as a host or a dopant in the light emitting layer.

[0260] In addition to the heterocyclic compound described above, the light-emitting layer may further include a host, an auxiliary dopant, a photosensitizer, a delayed fluorescent substance or any combination thereof. Each of the host, the auxiliary dopant, the photosensitizer, the delayed fluorescent substance or any combination thereof may include at least one deuterium.

[0261] For example, the light-emitting layer may include the heterocyclic compound and the host. The host and the heterocyclic compound are different from each other, and the host may also include an electron transport compound, a hole transport compound, a bipolar compound or any combination thereof. The host may not include a metal. The electron transport compound, the hole transport compound and the bipolar compound are different from each other.

[0262] According to an implementation example, the light-emitting layer may include the heterocyclic compound and the host, and the host may include an electron transport compound and a hole transport compound.

[0263] According to an implementation example, the electron transport compound and the hole transport compound may form an exciplex.

[0264] The thickness of the light-emitting layer may be about to about (For example, about to about ). When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be exhibited without substantially increasing the driving voltage.

[0265] [main body]

[0266] The host may include a compound represented by the following chemical formula 301:

[0267] <Chemical Formula 301>

[0268] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0269] In the chemical formula 301,

[0270] Ar 301 and L 301 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0271] xb11 is 1, 2 or 3,

[0272] xb1 is an integer from 0 to 5,

[0273] R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, or is replaced by at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkynyl, with at least one R 10aSubstituted or unsubstituted C 1 -C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0274] xb21 is an integer from 1 to 5,

[0275] Q 301 To Q 303 For the description of Q 1 Description.

[0276] For example, when xb11 in the chemical formula 301 is 2 or more, two or more Ar 301 Can be connected to each other by a single key.

[0277] As another example, the main body may include a compound represented by the following chemical formula 301-1, a compound represented by the following chemical formula 301-2, or any combination thereof:

[0278] <Chemical Formula 301-1>

[0279]

[0280] <Chemical formula 301-2>

[0281]

[0282] In the chemical formula 301-1 and the chemical formula 301-2,

[0283] Ring A 301 To Ring A 304 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0284] X 301 O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0285] xb22 and xb23 are independently 0, 1 or 2,

[0286] For L 301 , xb1 and R 301 Please refer to the description in this manual for details.

[0287] For L 302 To L 304 The descriptions of L are independently referred to 301 Description,

[0288] The descriptions of xb2 to xb4 refer independently to the description of xb1.

[0289] R 302 To R 305 and R 311 To R 314 For the description, refer to the R 301 Description.

[0290] As another example, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., compound H55 described below), a Mg complex, a Zn complex, or any combination thereof.

[0291] As another example, the host may include one of the following compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN: 9,10-di(2-naphthyl)anthracene), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN: 2-methyl-9,10-bis(naphthalen-2-yl)anthracene), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN: 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene thyl)-2-t-butyl-anthracene), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP: 4,4'-bis(N-carbazolyl)-1,1'-biphenyl), 1,3-di-9-carbazolylbenzene (mCP: 1,3-di-9-carbazolylbenzene), 1,3,5-tri(carbazol-9-yl)benzene (TCP: 1,3,5-tri(carbazol-9-yl)benzene) or any combination thereof:

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] According to an implementation example, the host may include a first host compound and a second host compound.

[0300] According to an implementation example, the first host compound may be a hole transporting host.

[0301] According to an implementation example, the second host compound may be an electron transporting host.

[0302] According to an implementation example, the “hole transporting host” may be a compound including a hole transporting moiety.

[0303] According to one embodiment, the “electron transporting host” is not only a compound including an electron transporting portion but may also be a compound having a bipolar property.

[0304] In this specification, "hole transporting host" and "electron transporting host" can be understood based on the relative difference between the hole mobility and the electron mobility. For example, even if the electron transporting host does not include an electron transporting part, in the case of a bipolar compound that exhibits a relatively high electron mobility compared to the hole transporting host, it can also be understood as an electron transporting host.

[0305] According to an implementation example, the hole transporting host can be represented by any one of the following chemical formulas 311-1 to 311-6, and the electron transporting host can be represented by any one of the following chemical formulas 312-1 to 312-4 and 313.

[0306] <Chemical formula 311-1>

[0307]

[0308] <Chemical formula 311-2>

[0309]

[0310] <Chemical formula 311-3>

[0311]

[0312] <Chemical formula 311-4>

[0313]

[0314] <Chemical formula 311-5>

[0315]

[0316] <Chemical formula 311-6>

[0317]

[0318] <Chemical formula 312-1>

[0319]

[0320] <Chemical formula 312-2>

[0321]

[0322] <Chemical formula 312-3>

[0323]

[0324] <Chemical formula 312-4>

[0325]

[0326] <Chemical formula 313>

[0327]

[0328] <Chemical formula 313A>

[0329]

[0330] In the chemical formulas 311-1 to 311-6, the chemical formulas 312-1 to 312-4, the chemical formula 313, and the chemical formula 313A,

[0331] Ar 301 For at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0332] A 301 To A 304 Independently of each other, C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0333] X 301 O, S, N[(L 304 ) xb4 -R 304 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],

[0334] X 302 , Y 301 and Y 302 are independently single bonds, O, S, N-[(L 305 ) xb5 -R 305 ]、C[(L 304 )xb4 -R 304 ][(L 305 ) xb5 -R 305 ]、Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O) 2 ,

[0335] xb1 to xb5 are 0, 1, 2, 3, 4, or 5,

[0336] xb6 is 1, 2, 3, 4, or 5,

[0337] X 321 To X 328 are independently N or C[(L 324 ) xb24 -R 324 ],

[0338] Y 321 For *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*'、*-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=C[(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=N-*'or*-N=C[(L 326 ) xb26 -R 326 ]-*',

[0339] k21 is 0, 1 or 2. When k21 is 321 does not exist,

[0340] xb21 to xb26 are independently 0, 1, 2, 3, 4 or 5,

[0341] A 31 , A 32 and A 34 Independently of each other, C3 -C 60 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0342] A 33 is a group represented by the chemical formula 313A,

[0343] X 31 N[(L 335 ) xb35 -(R 335 )]、O、S、Se、C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )],

[0344] xb31 to xb36 are independently 0, 1, 2, 3, 4 or 5,

[0345] xb42 to xb44 are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

[0346] L 301 To L 306 , L 321 to L326 and L 331 To L 336 are independently single bonds, are 10a Substituted or unsubstituted C 1 -C 20 Alkylene, with at least one R 10a Substituted or unsubstituted C 2 -C 20 Alkenylene, with at least one R 10a Substituted or unsubstituted C 2 -C 20 Alkyne, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkylene, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, with at least one R 10a Substituted or unsubstituted C 3-C 10 Cycloalkenylene, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Arylene, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroarylene, with at least one R 10a A substituted or unsubstituted divalent non-aromatic condensed polycyclic group or a ... 10a a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0347] R 301 To R 305 , R 311 To R 314 , R 321 To R 324 and R 331 To R 336 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted by at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C 2 -C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C 3 -C 10 Cycloalkenyl, with at least one R 10a Substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C 6 -C60 Aryl, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C 6 -C 60 Arylthio, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroaryl, with at least one R 10a Substituted or unsubstituted C 1- C 60 Heteroaryloxy, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heteroarylthio, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a Substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) or -P(=S)(Q 1 )(Q 2 ),

[0348] R 321 To R 324 Two or more adjacent substituents in the formula (R) may be optionally combined with each other to form a 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0349] The R 10a for,

[0350] Deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

[0351] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0352] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy, C1 -C 60 Heteroarylthio, Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy or C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryloxy or C 1 -C 60 heteroarylthio; or

[0353] Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 )

[0354] Or P(=O)(Q 31 )(Q 32 ),

[0355] The Q 11 To the Q 13 Q 21 To the Q 23 Q 31 To the Q 33 Q 41 To the Q 43 Q 301 To the Q 303 Q 321 To the Q 323 And the Q 331 To the Q 333independently of each other are hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or deuterated, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.

[0356] According to an implementation example, the first host compound and the second host compound can form an exciplex.

[0357] [Phosphorescent dopant]

[0358] According to an implementation example, the light-emitting layer may further include a phosphorescent dopant.

[0359] For example, the light-emitting layer further includes a phosphorescent dopant, and the phosphorescent dopant can function as a photosensitizer.

[0360] The phosphorescent dopant may include at least one transition metal as a central metal.

[0361] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

[0362] The phosphorescent dopant may be electrically neutral.

[0363] According to an implementation example, the phosphorescent dopant may be an organic metal compound.

[0364] According to an implementation example, the phosphorescent dopant may include an organic metal compound represented by the following chemical formula 401:

[0365] <Chemical Formula 401>

[0366] M(L 401 ) xc1 (L 402 ) xc2 ;

[0367] <Chemical Formula 402>

[0368]

[0369] In the chemical formula 401 and the chemical formula 402,

[0370] M is a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0371] L 401 is a ligand represented by the chemical formula 402, xc1 may be 1, 2 or 3, wherein when xc1 is 2 or more, two or more L 401 Same or different from each other,

[0372] L 402 is an organic ligand, xc2 is 0, 1, 2, 3 or 4, and when xc2 is 2 or more, two or more L 402 Same or different from each other,

[0373] X 401 and X 402 independently of each other is nitrogen or carbon,

[0374] Ring A 401 and Ring A 402 Independently of each other, C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0375] T 401 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*',

[0376] *-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*',

[0377] X 403 and X 404 are independently chemical bonds (e.g., covalent bonds or coordination bonds), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q413 )(Q 414 ),

[0378] Regarding the Q 411 To the Q 414 For the description of Q 1 Description,

[0379] R 401 and R 402 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 10a Substituted or unsubstituted C 1 -C 20 Alkyl, with at least one R 10a Substituted or unsubstituted C 1 -C 20 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0380] Regarding the Q 401 To the Q 403 For the description of Q 1 Description,

[0381] xc11 and xc12 are independently an integer from 0 to 10,

[0382] * and *' in the chemical formula 402 are binding sites for M in the chemical formula 401, respectively.

[0383] For example, in the chemical formula 402, i) X 401 It can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 Both may be nitrogen.

[0384] As another example, in the chemical formula 401, when xc1 is 2 or more, two or more L 401 The two rings A 401 Optionally, through T as a linker 402 Connected to each other, or two rings A 402 Selectively through T as a linker 403 are connected to each other (see compounds PD1 to PD4 and compound PD7 below). 402 and T 403 For the description of T 401 Description.

[0385] In the chemical formula 401, L 402 It can be any organic ligand. For example, the L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.

[0386] The phosphorescent dopant may include, for example, one of the following compounds PD1 to PD41 or any combination thereof:

[0387]

[0388]

[0389]

[0390] [Fluorescent dopant]

[0391] According to an implementation example, the light-emitting layer may further include a fluorescent dopant.

[0392] The fluorescent dopant may include an amine-containing compound, a styrene-containing compound, or any combination thereof.

[0393] For example, the fluorescent dopant may include a compound represented by the following Chemical Formula 501:

[0394] <Chemical Formula 501>

[0395]

[0396] In the chemical formula 501,

[0397] Ar 501, L 501 To L 503 , R 501 and R 502 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0398] xd1 to xd3 are independently 0, 1, 2 or 3, and

[0399] xd4 can be 1, 2, 3, 4, 5 or 6.

[0400] For example, in the chemical formula 501, Ar 501 It may include a condensed ring group in which three or more monocyclic groups are condensed with each other (for example, anthracene groups, group or pyrene group, etc.).

[0401] As another example, in the chemical formula 501, xd4 may be 2.

[0402] For example, the fluorescent dopant may include one of the following compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

[0403]

[0404]

[0405]

[0406] [Delayed fluorescent substance]

[0407] According to an implementation example, the light-emitting layer may further include a delayed fluorescent substance.

[0408] In the present specification, the delayed fluorescent substance can be selected from any compound that can emit delayed fluorescence based on a delayed fluorescence emission mechanism.

[0409] The delayed fluorescent substance included in the light emitting layer may function as a host or a dopant according to the kind of other substances included in the light emitting layer.

[0410] According to an implementation example, the difference between the triplet energy level (eV) of the delayed fluorescent substance and the singlet energy level (eV) of the delayed fluorescent substance may be greater than 0 eV and less than 0.5 eV. By making the difference between the triplet energy level (eV) of the delayed fluorescent substance and the singlet energy level (eV) of the delayed fluorescent substance satisfy the above range, the reverse energy transfer (up-conversion) from the triplet state to the singlet state in the delayed fluorescent substance can be effectively achieved, thereby improving the luminous efficiency of the organic light-emitting element 10, etc.

[0411] For example, the delayed fluorescent material may include: i) at least one electron donor (eg, a π-electron-rich C 3 -C 60 Cyclic groups (πelectron-rich C 3 -C 60 cyclic group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π-electron-poor nitrogen-containing C 1 -C 60 Cyclic group (πelectron-deficientnitrogen-containing C 1 -C 60 ii) a substance comprising two or more cyclic groups condensed with a common boron (B) 8 -C 60 Substances with polycyclic groups, etc.

[0412] Examples of the delayed fluorescent substance may include at least one of the following compounds DF1 to DF9:

[0413]

[0414] [Quantum dot]

[0415] The light emitting layer may include quantum dots.

[0416] In this specification, a quantum dot refers to a crystal of a semiconductor compound, and may include any substance that can emit light of various wavelengths depending on the size of the crystal.

[0417] The diameter of the quantum dots may be, for example, about 1 nm to 10 nm.

[0418] The quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or a process similar to these processes.

[0419] The wet chemical process is a method of growing quantum dot particle crystals after mixing an organic solvent and a precursor substance. When the crystal grows, the organic solvent acts as a dispersant that naturally coordinates on the surface of the quantum dot crystal and regulates the growth of the crystal, so the growth of quantum dot particles can be controlled by utilizing a process that is easier and less expensive than vapor deposition methods such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).

[0420] The quantum dots may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, Group IV elements or compounds, or any combination thereof.

[0421] Examples of the II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, C CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.

[0422] Examples of the III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. In addition, the III-V semiconductor compounds may also include Group II elements. Examples of the Group III-V semiconductor compound also including the Group II element may include InZnP, InGaZnP, InAlZnP, and the like.

[0423] Examples of the III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 , InTe, etc.; ternary compounds such as InGaS 3 、InGaSe 3 etc.; or any combination thereof.

[0424] Examples of the I-III-VI group semiconductor compounds may include ternary compounds such as AgInS, AgInS 2 、CuInS、CuInS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 etc. or any combination thereof.

[0425] Examples of the IV-VI group semiconductor compounds may include: binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.

[0426] The Group IV elements or compounds may include: single elements, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.

[0427] Each element included in the multi-component compound such as the binary compound, the ternary compound, and the quaternary compound may exist in particles at a uniform concentration or a non-uniform concentration.

[0428] In addition, the quantum dot may have a single structure in which the concentration of each element included in the corresponding quantum dot is uniform or a core-shell dual structure. For example, a substance included in the core and a substance included in the shell may be different from each other.

[0429] The shell of the quantum dot may perform the role of a protective layer for preventing the chemical denaturation of the core and maintaining semiconductor properties and / or a charging layer for imparting electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell gradually decreases toward the center.

[0430] Examples of the shell of the quantum dot may include metal, metalloid or non-metal oxides, semiconductor compounds or combinations thereof. Examples of the metal, metalloid or non-metal oxides may include binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 , NiO, etc.; ternary compounds such as MgAl 2 O 4 、CoFe2 O 4 、NiFe 2 O 4 、CoMn 2 O 4 etc.; or any combination thereof. Examples of the semiconductor compound may include II-VI semiconductor compounds, III-V semiconductor compounds, III-VI semiconductor compounds, I-III-VI semiconductor compounds, IV-VI semiconductor compounds, or any combination thereof as described in this specification. For example, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0431] The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less (specifically about 40 nm or less, more specifically about 30 nm or less), and within this range, the color purity or color reproducibility may be improved. In addition, the light emitted by such quantum dots is emitted in all directions, and therefore, the wide viewing angle may be improved.

[0432] In addition, the quantum dots may be in the form of spherical, pyramidal, multi-arm or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, and the like.

[0433] By adjusting the size of the quantum dots, the energy band gap can be adjusted, so that light of multiple wavelength bands can be obtained in the quantum dot light-emitting layer. Therefore, by using quantum dots of different sizes, an organic light-emitting element that emits light of multiple wavelengths can be realized. Specifically, the size of the quantum dots can be selected to be able to emit red light, green light and / or blue light. In addition, the size of the quantum dots can be configured so that multiple colors of light are combined to emit white light.

[0434] [Electron Transport Region in Intermediate Layer 130]

[0435] The electron transport region may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing a plurality of substances different from each other; or iii) a multi-layer structure including a plurality of layers containing a plurality of substances different from each other.

[0436] The electron transport region may include a buffer layer, a hole blocking layer, an electron regulating layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0437] For example, the electron transport region may have a structure of an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron regulating layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are stacked in sequence starting from the light-emitting layer.

[0438] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron regulating layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C 1 -C 60 Cyclic groups (πelectron-deficient nitrogen-containing C 1 -C 60 cyclic group) of metal-free compounds.

[0439] For example, the electron transport region may include a compound represented by the following Chemical Formula 601.

[0440] <Chemical Formula 601>

[0441] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0442] In the chemical formula 601,

[0443] Ar 601 and L 601 Independently of each other, at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0444] xe11 is 1, 2 or 3,

[0445] xe1 is 0, 1, 2, 3, 4, or 5,

[0446] R 601 For at least one R 10a Substituted or unsubstituted C 3 -C 60A carbocyclic group, with at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),

[0447] Regarding the Q 601 To Q 603 For the description of Q 1 Description,

[0448] xe21 is 1, 2, 3, 4 or 5,

[0449] The Ar 601 , L 601 and R 601 At least one of them can be independently selected from at least one R 10a Substituted or unsubstituted π-electron-poor nitrogen-containing C 1 -C 60 Ring group.

[0450] For example, in the chemical formula 601, when xe11 is 2 or more, two or more Ar 601 Can be connected to each other by a single key.

[0451] As another example, in the chemical formula 601, Ar 601 The anthracene group may be substituted or unsubstituted.

[0452] As another example, the electron transport region may include a compound represented by the following chemical formula 601-1:

[0453] <Chemical Formula 601-1>

[0454]

[0455] In the chemical formula 601-1,

[0456] X 614 N or C(R 614 ), X 615 N or C(R 615 ), X 616 N or C(R 616 ), X 614 To X 616At least one of them is N,

[0457] For L 611 To L 613 For the description of L 601 Description,

[0458] For the description of xe611 to xe613, refer to the description of xe1.

[0459] R 611 To R 613 For the description, refer to the R 601 Description,

[0460] R 614 To R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, with at least one R 10a Substituted or unsubstituted C 3 -C 60 A carbocyclic group or a group consisting of at least one R 10a Substituted or unsubstituted C 1 -C 60 Heterocyclic group.

[0461] For example, in the chemical formula 601 and the chemical formula 601-1, xe1 and xe611 to xe613 may be 0, 1 or 2 independently of each other.

[0462] The electron transport region may include one of the following compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), Alq 3 , BAlq, TAZ, NTAZ or any combination thereof:

[0463]

[0464]

[0465]

[0466] The thickness of the electron transport region may be about to about (For example, about to about ). In the case where the electron transport region includes a buffer layer, a hole blocking layer, an electron regulating layer, an electron transport layer or any combination thereof, the thickness of the buffer layer, the hole blocking layer or the electron regulating layer may be independently about to about (For example, about to about ), the thickness of the electron transport layer may be about to about (For example, about to about ). When the thickness of the buffer layer, the hole blocking layer, the electron regulating layer, the electron transport layer and / or the electron transport region satisfies the above-mentioned range, satisfactory electron transport characteristics can be obtained without substantially increasing the driving voltage.

[0467] The electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing substance in addition to the substances described above.

[0468] The metal-containing substance may include an alkali metal complex, an alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion or a Cs ion, and the metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion or a Ba ion. The ligands coordinated with the metal ions of the alkali metal complex and the alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0469] For example, the metal-containing substance may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (LiQ) or compound ET-D2:

[0470]

[0471] The electron transport region may include an electron injection layer that easily injects electrons from the second electrode 150. The electron injection layer may directly contact the second electrode 150.

[0472] The electron injection layer may have the following structures: i) a single-layer structure consisting of a single layer composed of a single substance; ii) a single-layer structure consisting of a single layer containing multiple different substances; or iii) a multi-layer structure having multiple layers containing multiple different substances.

[0473] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0474] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0475] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively, or any combination thereof.

[0476] The alkali metal compound may include alkali metal oxides such as Li 2 O, Cs 2 O, K 2 O, etc., alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or any combination thereof. The alkaline earth metal compound may include alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying 0 < x < 1), Ba x Ca 1-x O (x is a real number satisfying 0 < x < 1), etc. The rare earth metal compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 、TbF 3 、YbI 3 、ScI 3 、TbI 3Or any combination thereof. Alternatively, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 2 Te 3 、Ce 2 Te 3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 、Lu 2 Te 3 wait.

[0477] The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex may include: i) one of the ions of the alkali metal, alkaline earth metal and rare earth metal as described above; and ii) a ligand bound to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.

[0478] The electron injection layer may be composed solely of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above, or may also include an organic substance (e.g., a compound represented by the chemical formula 601).

[0479] According to an implementation example, the electron injection layer may be i) composed of an alkali metal compound (e.g., an alkali metal halide), or ii) composed of a) an alkali metal compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, a LiF:Yb co-deposition layer, etc.

[0480] In the case where the electron injection layer also includes organic matter, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or unevenly dispersed in the matrix including the organic matter.

[0481] The thickness of the electron injection layer may be about to about about to about When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

[0482] [Second electrode 150]

[0483] The second electrode 150 is disposed on the upper portion of the intermediate layer 130. The second electrode 150 may be a cathode as an electron injection electrode, and in this case, a metal, alloy, conductive compound or any combination thereof having a low work function may be used as the material for the second electrode 150.

[0484] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.

[0485] The second electrode 150 may have a single-layer structure of a single layer or a multi-layer structure including a plurality of layers.

[0486] [Overlay]

[0487] The first covering layer may be arranged outside the first electrode 110, and / or the second covering layer may be arranged outside the second electrode 150. Specifically, the organic light emitting element 10 may have: a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in sequence; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence; or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second covering layer are stacked in sequence.

[0488] Light generated in the light-emitting layer in the intermediate layer 130 of the organic light-emitting element 10 can be extracted toward the outside through the first electrode 110 as a semi-transmissive electrode or a transmissive electrode and the first covering layer, and light generated in the light-emitting layer in the intermediate layer 130 of the organic light-emitting element 10 can be extracted toward the outside through the second electrode 150 as a semi-transmissive electrode or a transmissive electrode and the second covering layer.

[0489] The first covering layer and the second covering layer can increase the external light emitting efficiency according to the principle of constructive interference. Thus, the light extraction efficiency of the organic light emitting element 10 is increased, so that the light emitting efficiency of the organic light emitting element 10 can be improved.

[0490] Each of the first cover layer and the second cover layer may include a substance having a refractive index (at 589 nm) of about 1.6 or more.

[0491] The first covering layer and the second covering layer may be independently an organic covering layer including an organic substance, an inorganic covering layer including an inorganic substance, or an organic-inorganic composite covering layer including an organic substance and an inorganic substance.

[0492] At least one of the first covering layer and the second covering layer may independently include carbocyclic compounds, heterocyclic compounds, amine-containing compounds, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes or any combination thereof. The carbocyclic compounds, heterocyclic compounds and amine-containing compounds may be selectively substituted with substituents containing O, N, S, Se, Si, F, Cl, Br, I or any combination thereof. According to an implementation example, at least one of the first covering layer and the second covering layer may independently include amine-containing compounds.

[0493] For example, at least one of the first cover layer and the second cover layer may independently include the compound represented by the Chemical Formula 201, the compound represented by the Chemical Formula 202, or any combination thereof.

[0494] According to another implementation example, at least one of the first covering layer and the second covering layer may independently include one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any combination thereof:

[0495]

[0496] [film]

[0497] The organometallic compound represented by the chemical formula 1 may be included in various films. Therefore, according to another aspect, a film including the organometallic compound represented by the chemical formula 1 and / or the heterocyclic compound represented by the chemical formula 2 may be provided. The film may be, for example, an optical component (or light control unit) (e.g., a color filter, a color conversion component, a cover layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarization layer, a quantum dot content layer, etc.), a light shielding component (e.g., a light reflection layer, a light absorption layer, etc.), a protective component (e.g., an insulating layer, a dielectric layer, etc.), etc.

[0498] [Electronic devices]

[0499] The organic light emitting element 10 may be included in various electronic devices. For example, the electronic device including the organic light emitting element 10 may be a light emitting device, an authentication device, and the like.

[0500] In addition to the organic light emitting element 10, the light emitting device (e.g., a display device) may further include: i) a color filter; ii) a color conversion layer; or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in the traveling direction of at least one of the lights emitted from the organic light emitting element 10. For example, the light emitted from the organic light emitting element 10 may be blue light or white light. The description of the organic light emitting element 10 refers to the above description. According to an implementation example, the color conversion layer may include quantum dots. The quantum dots may be, for example, the same quantum dots as those described in this specification.

[0501] The electronic device may include a first substrate, the first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.

[0502] The pixel definition film is disposed between the plurality of sub-pixel regions to define each sub-pixel region.

[0503] The color filter may further include a plurality of color filter regions and a light blocking pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light blocking pattern disposed between the plurality of color conversion regions.

[0504] The plurality of color filter regions (or plurality of color conversion regions) include: a first region emitting a first color light; a second region emitting a second color light; and / or a third region emitting a third color light, wherein the first color light, the second color light and / or the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or plurality of color conversion regions) may include quantum dots. Specifically, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. For the description of quantum dots, refer to the description in this specification. Each of the first region, the second region and / or the third region may also include a scatterer.

[0505] For example, the organic light emitting element 10 may emit the first light, the first region may absorb the first light and emit the first-1 color light, the second region may absorb the first light and emit the second-1 color light, and the third region may absorb the first light and emit the third-1 color light. At this time, the first-1 color light, the second-1 color light, and the third-1 color light may have different maximum emission wavelengths from each other. Specifically, the first light may be blue light, the first-1 color light may be red light, the second-1 color light may be green light, and the third-1 color light may be blue light.

[0506] In addition to the organic light emitting element 10 described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode 110 and the second electrode 150 of the organic light emitting element 10.

[0507] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.

[0508] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

[0509] The electronic device may further include a sealing portion for sealing the organic light emitting element 10. The sealing portion may be arranged between the color filter and / or the color conversion layer and the organic light emitting element 10. The sealing portion may allow light from the organic light emitting element 10 to be extracted to the outside while preventing external air and moisture from penetrating into the organic light emitting element 10. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including one or more organic layers and / or inorganic layers. In the case where the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0510] In addition to the color filter and / or color conversion layer, various functional layers may be additionally arranged on the sealing portion according to the purpose of the electronic device. The functional layers may include a touch screen layer, a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.

[0511] The authentication device may further include a biometric information collection unit in addition to the organic light emitting element 10. The authentication device may be, for example, a biometric authentication device for authenticating an individual by using biometric information of a living being (eg, fingertips, pupils, etc.).

[0512] The electronic device can be applied to various displays, light sources, lighting, personal computers (for example, mobile personal computers), portable phones, digital cameras, electronic manuals, electronic dictionaries, electronic game consoles, medical instruments (for example, electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram display devices, ultrasonic diagnostic devices, endoscope display devices), fish finders, various measuring instruments, instruments (for example, instruments used in vehicles, aircraft, and ships), projectors, etc.

[0513] [against Figure 2 and Figure 3 Description]

[0514] Figure 2 is a cross-sectional view of a light emitting device according to an implementation example of the present invention.

[0515] Figure 2 The light emitting device includes a substrate 100, a thin film transistor TFT, an organic light emitting element, and a packaging part 300 for sealing the organic light emitting element.

[0516] The substrate 100 may be a flexible substrate, a glass substrate or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 prevents impurities from penetrating through the substrate 100 and provides a flat surface on the upper portion of the substrate 100.

[0517] A thin film transistor TFT may be disposed on the buffer layer 210. The thin film transistor TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0518] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and include a source region, a drain region, and a channel region.

[0519] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the upper portion of the active layer 220 , and the gate electrode 240 may be disposed on the upper portion of the gate insulating film 230 .

[0520] The interlayer insulating film 250 may be disposed on the upper portion of the gate electrode 240. The interlayer insulating film 250 is disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270, respectively, so as to insulate the gate electrode 240 from the source electrode 260 and the gate electrode 240 from the drain electrode 270.

[0521] The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to contact the exposed source region and the drain region of the active layer 220.

[0522] The thin film transistor TFT as described above can be electrically connected to the organic light emitting element to drive the organic light emitting element, and can be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The organic light emitting element may be disposed on the passivation layer 280. The organic light emitting element includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0523] The first electrode 110 may be disposed on the passivation layer 280 . The passivation layer 280 does not completely cover the drain electrode 270 but is disposed in a manner of exposing a predetermined region of the drain electrode 270 , and the first electrode 110 may be disposed to be connected to the exposed drain electrode 270 .

[0524] A pixel defining film 290 including an insulator may be disposed on the first electrode 110. The pixel defining film 290 exposes a predetermined region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic organic film. Although not shown in the figure Figure 2 , but more than a portion of the intermediate layer 130 may extend to the upper portion of the pixel defining film 290 and be arranged in the form of a common layer.

[0525] The second electrode 150 may be disposed on the intermediate layer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0526] The encapsulation unit 300 may be disposed on the cover layer 170. The encapsulation unit 300 may be disposed on the organic light emitting element and has the function of protecting the organic light emitting element from moisture or oxygen. The encapsulation unit 300 may include: an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or a combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE: aliphatic glycidyl ether)), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0527] Figure 3 is a cross-sectional view of a light emitting device according to another implementation example of the present invention.

[0528] In addition to the fact that the light blocking pattern 500 and the functional region 400 are additionally arranged on the upper portion of the packaging portion 300, Figure 3 The light emitting device and Figure 2 The functional region 400 may be: i) a color filter region; ii) a color conversion region; or iii) a combination of a color filter region and a color conversion region. Figure 3 The organic light-emitting elements of the light-emitting device may be tandem organic light-emitting elements.

[0529] [against Figure 4 Description]

[0530] Figure 41 is a perspective view schematically illustrating an electronic device 1 including an organic light-emitting element according to an implementation example of the present invention. The electronic device 1, as a device for displaying moving images or still images, can be not only a portable electronic device such as a mobile phone, a smart phone, a tablet personal computer, a mobile communication terminal, an electronic manual, an electronic book, a portable multimedia player (PMP: portable multimedia player) or a navigator, an ultra-portable mobile personal computer (UMPC: Ultra Mobile PC), but also a variety of products such as a television, a laptop computer, a monitor, a billboard, or an Internet of Things (IOT: internet of things) device, or a part thereof. In addition, the electronic device 1 can be a wearable device (wearable device) such as a smart watch (smartwatch), a watch phone (watch phone), a glasses-type display, or a head mounted display (HMD: head mounted display), or a part thereof. Of course, the present invention is not limited to this. For example, the electronic device 1 may include a center information display (CID) arranged on the dashboard of the car and the center fascia or instrument panel of the car, a room mirror display (room mirror display) replacing the side mirrors of the vehicle, an entertainment device for the rear seat of the vehicle or a display arranged on the back of the front seat, a head-up display (HUD) set in front of the vehicle or projected on the front windshield, and a holographic augmented reality head-up display (CGH AR HUD: Computer Generated Hologram Augmented Reality HeadUp Display). For the sake of explanation, Figure 4 The case where the electronic device 1 is a smart phone is shown in the figure.

[0531] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image by an array of a plurality of pixels two-dimensionally arranged in the display area DA.

[0532] The non-display area NDA, as an area where no image is displayed, may surround the display area DA as a whole. A driver or the like for providing an electrical signal or power to a display element arranged in the display area DA may be arranged in the non-display area NDA. A pad as an area capable of electrically connecting an electronic element or a printed circuit board or the like may be arranged in the non-display area NDA.

[0533] The length of the electronic device 1 in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 As shown, the length in the x-axis direction may be shorter than the length in the y-axis direction. In another example, the length in the x-axis direction may be the same as the length in the y-axis direction. In another example, the length in the x-axis direction may be longer than the length in the y-axis direction.

[0534] [against Figure 5 and Figures 6a to 6c Description]

[0535] Figure 5 1 is a diagram schematically illustrating the exterior of a vehicle 1000 as an electronic device including an organic light emitting element according to an implementation example of the present invention. Figures 6a to 6c 1 is a diagram schematically illustrating the interior of a vehicle 1000 according to various implementation examples of the present invention.

[0536] Reference Figure 5 , Figure 6a , Figure 6b as well as Figure 6c The vehicle 1000 may represent a variety of devices that move a transported object such as a person, an object, or an animal from a starting point to a destination. The vehicle 1000 may include a vehicle that travels on a road or track, a ship that moves on the sea or a river, and an airplane that flies in the sky using the action of air.

[0537] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include a three-wheeled vehicle or a four-wheeled vehicle, an engineering machine, a two-wheeled vehicle, a prime mover device, a bicycle, and a train traveling on a track.

[0538] The vehicle 1000 may include a body having internal devices and external devices, and a chassis provided with mechanical devices required for driving as the remaining parts other than the body. The external devices of the body may include a front guard plate, an engine cover, a roof plate, a rear guard plate, a trunk, and pillars provided at the boundaries between doors. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a travel device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear left and right wheels, etc.

[0539] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster 1400 , a center instrument panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .

[0540] The side window glass 1100 and the front window glass 1200 may be divided by pillars disposed between the side window glass 1100 and the front window glass 1200 .

[0541] The side window glass 1100 may be disposed on the side of the vehicle 1000. In one embodiment, the side window glass 1100 may be disposed on the door of the vehicle 1000. The side window glass 1100 may be provided in a plurality and may face each other. In one embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In one embodiment, the first side window glass 1110 may be arranged adjacent to the cluster 1400. The second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.

[0542] In one embodiment, the side window glass 1100 may be spaced apart from each other along the x-axis direction or the -x-axis direction. For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other along the x-axis direction or the -x-axis direction. In other words, the virtual straight line L connecting the side window glass 1100 may extend along the x-axis direction or the -x-axis direction. For example, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend along the x-axis direction or the -x-axis direction.

[0543] The front window glass 1200 may be provided in front of the vehicle 1000. The front window glass 1200 may be arranged between the side window glasses 1100 facing each other.

[0544] The side mirror 1300 can provide a rear view of the vehicle 1000. The side mirror 1300 can be set on an external device of the vehicle body. In an implementation example, the side mirror 1300 can be equipped in multiples. One of the multiple side mirrors 1300 can be arranged on the outside of the first side window glass 1110. Another of the multiple side mirrors 1300 can be arranged on the outside of the second side window glass 1120.

[0545] Cluster 1400 may be located in front of the steering wheel. Cluster 1400 may be arranged with a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a direction change indicator light, a high beam indicator light, a warning light, a seat belt warning light, an odometer, a driving recorder, an automatic transmission selector lever indicator light, a door open warning light, an oil warning light, and / or a low fuel warning light.

[0546] The center instrument panel 1500 may include a control panel on which a plurality of buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center instrument panel 1500 may be arranged at one side of the cluster 1400 .

[0547] The passenger seat instrument panel 1600 may be separated from the cluster 1400 via the center instrument panel 1500. In one embodiment, the cluster 1400 may be arranged corresponding to the driver's seat (not shown), and the passenger seat instrument panel 1600 may be arranged corresponding to the passenger seat (not shown). In one implementation example, the cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.

[0548] In one embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In one embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged in at least any one of the cluster 1400, the center instrument panel 1500, and the passenger seat instrument panel 1600.

[0549] The display device 2 may include an organic light emitting display device (Organic Light Emitting Display Device), an inorganic electroluminescent (EL) display device (Inorganic Electroluminescent Display Device), a quantum dot display device (Quantum dot display Device), etc. In the following, the display device 2 according to an implementation example of the present invention is described by taking an organic light emitting display device including an organic light emitting element according to the present invention as an example, but in the embodiments of the present invention, a display device in a variety of ways as described above may be used.

[0550] Reference Figure 6a , the display device 2 may be arranged in the center instrument panel 1500. In one implementation example, the display device 2 may display navigation information. In one implementation example, the display device 2 may display information related to audio, video or vehicle settings.

[0551] Reference Figure 6b , the display device 2 may be arranged in the cluster 1400. In this case, the cluster 1400 may display operation information and the like by means of the display device 2. That is, the cluster 1400 may be implemented in a digital manner. The digital cluster 1400 may display vehicle information and driving information as an image. For example, the needle and gauge of the tachometer and various warning light icons may be displayed by means of digital signals.

[0552] Reference Figure 6c, the display device 2 may be arranged in the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or located on the passenger seat instrument panel 1600. In one implementation example, the display device 2 arranged in the passenger seat instrument panel 1600 may display images related to the information displayed on the cluster 1400 and / or the information displayed on the center instrument panel 1500. In another embodiment, the display device 2 arranged in the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster 1400 and / or the information displayed on the center instrument panel 1500.

[0553] [Preparation method]

[0554] The various layers included in the hole transport region, the light-emitting layer, and the various layers included in the electron transport region can be formed in predetermined regions by using a variety of methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB: Langmuir-Blodgett) method, inkjet printing, laser printing, laser thermal transfer (LITI: Laser Induced Thermal Imaging), etc.

[0555] In the case of forming the various layers included in the hole transport region, the light emitting layer, and the various layers included in the electron transport region by a vacuum deposition method, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and about to about Within the deposition rate range of , the deposition conditions are selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed.

[0556] [Definition of terms]

[0557] In this manual, C 3 -C 60 A carbocyclic group refers to a ring group having 3 to 60 carbon atoms and composed only of carbon atoms. 1 -C 60 The heterocyclic group refers to a ring group having 1 to 60 carbon atoms and including heteroatoms as ring atoms in addition to carbon. 3 -C 60 Carbocyclic groups and C 1 -C 60 The heterocyclic group may be a monocyclic group consisting of one ring or a polycyclic group consisting of two or more rings condensed with each other. 1 -C 60 The number of ring atoms in the heterocyclic group may be 3 to 61.

[0558] In this specification, the ring group includes the C 3 -C 60 Carbocyclic groups and C 1 -C 60 Both heterocyclic groups.

[0559] In this specification, the π-electron-rich C 3 -C 60 Cyclic groups (πelectron-rich C 3 -C 60 cyclic group) refers to a cyclic group with 3 to 60 carbon atoms that does not include *-N=*' as a ring-forming part, a nitrogen-containing C 1 -C 60 Cyclic groups (πelectron-deficient nitrogen-containing C 1 -C 60 The term "cyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a ring-forming part.

[0560] For example,

[0561] The C 3 -C 60 The carbocyclic group may be: i) a group T1; or ii) a condensed ring group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, a benzophenone group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),

[0562] The C 1 -C 60The heterocyclic group may be: i) a group T2; ii) a condensed ring group in which two or more groups T2 are condensed with each other; or iii) a condensed ring group in which one or more groups T2 and one or more groups T1 are condensed with each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiorrolecarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene ... a benzophenone group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, a benzothiazole group, a benzisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzo a quinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),

[0563] The π-electron-rich C 3 -C 60 The cyclic group may be: i) a group T1; ii) a condensed ring group in which two or more groups T1 are condensed with each other; iii) a group T3; iv) a condensed ring group in which two or more groups T3 are condensed with each other; or v) a condensed ring group in which one or more groups T3 and one or more groups T1 are condensed with each other (for example, the C 3 -C 60carbocyclic group, 1H-pyrrole group, thiol group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzoindole group, naphthoindole group, isoindole group, benzoisoindole group, naphthoisoindole group, benzothiol group, benzothiophene group, benzofuran group, carbazole group, dibenzothiol group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolecarbazole group, benzofurancarbazole group, benzothiophenecarbazole group, benzothiorrolocarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofurandibenzofuran group, benzofurandibenzothiophene group, benzothiophenedibenzothiophene group, etc.),

[0564] The π-electron-poor nitrogen-containing C 1 -C 60 The cyclic group may be: i) a group T4; ii) a condensed ring group in which two or more groups T4 are condensed with each other; iii) a condensed ring group in which one or more groups T4 and one or more groups T1 are condensed with each other; iv) a condensed ring group in which one or more groups T4 and one or more groups T3 are condensed with each other; or v) a condensed ring group in which one or more groups T4, one or more groups T1 and one or more groups T3 are condensed with each other (for example, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),

[0565] The group T1 is a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,

[0566] The group T2 is a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,

[0567] The group T3 is a furan group, a thiophene group, a 1H-pyrrole group, a thiole group or a borole group,

[0568] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.

[0569] In this specification, the terms cyclic group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic groups, π-electron-rich C 3 -C 60 Cyclic groups or π-electron-poor nitrogen-containing C 1 -C 60Cyclic group may refer to a group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) condensed with any cyclic group according to the structure of the chemical formula using the term. For example, a "phenyl group" may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person of ordinary skill in the art according to the structure of the chemical formula including the "phenyl group".

[0570] For example, the unit price C 3 -C 60 Carbocyclic groups and monovalent C 1 -C 60 Examples of heterocyclic groups may include 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 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group, divalent C 3 -C 60 Carbocyclic groups and divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 heteroarylene group, a divalent non-aromatic condensed polycyclic group and a divalent non-aromatic condensed heteropolycyclic group.

[0571] In this manual, C 1 -C 60The alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, and the like. 1 -C 60 Alkylene refers to a group having the same 1 -C 60 Alkyl is a divalent group of the same structure.

[0572] In this manual, C 2 -C 60 Alkenyl refers to 2 -C 60 The alkyl group is a monovalent hydrocarbon group having one or more carbon-carbon double bonds in the middle or at the end, and specific examples thereof include vinyl, propenyl, butenyl, etc. In this specification, C 2 -C 60 Alkenylene refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0573] In this manual, C 2 -C 60 Alkynyl refers to 2 -C 60 The alkyl group is a monovalent hydrocarbon group having one or more carbon-carbon triple bonds in the middle or at the end, and specific examples thereof include ethynyl, propynyl, etc. 2 -C 60 Alkyne refers to a group having 2 -C 60 Alkynyl is a divalent group of the same structure.

[0574] In this manual, C 1 -C 60 Alkoxy refers to a group having -OA 101 (Among them, A 101 It is the C 1 -C 60 Specific examples thereof include methoxy, ethoxy, isopropoxy and the like.

[0575] In this manual, C 3 -C 10Cycloalkyl refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like. In this specification, C 3 -C 10 Cycloalkylene refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0576] In this manual, C 1 -C 10 Heterocycloalkyl refers to a monovalent ring group having 1 to 10 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms, and specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. 1 -C 10 Heterocycloalkylene refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0577] In this manual, C 3 -C 10 Cycloalkenyl refers to a monovalent ring group having 3 to 10 carbon atoms, which means a group having at least one carbon-carbon double bond in the ring but not having aromaticity, and specific examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. In this specification, C 3 -C 10 Cycloalkenylene refers to 3 -C 10 The cycloalkenyl group has a divalent group of the same structure.

[0578] In this manual, C 1 -C 10 The heterocycloalkenyl group refers to a monovalent ring group having 1 to 10 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms, and having at least one double bond in the ring. 1 -C 10Specific examples of the heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. 1 -C 10 Heterocycloalkenylene refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0579] In this manual, C 6 -C 60 Aryl refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms. 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Specific examples of the aryl group include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, peryl, hexyl, pentyl, rubidinyl, coronenyl, ovalenyl, etc. In the C 6 -C 60 Aryl and C 6 -C 60 In the case where the arylene group includes two or more rings, the two or more rings may be condensed with each other.

[0580] In this manual, C 1 -C 60 The heteroaryl group refers to a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring atom in addition to carbon atoms. 1 -C 60 The heteroarylene group refers to a divalent group that includes at least one heteroatom as a ring-forming atom in addition to carbon atoms and has a heterocyclic aromatic system with 1 to 60 carbon atoms. 1 -C 60 Specific examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 In the case where the heteroarylene group includes two or more rings, the two or more rings may be condensed with each other.

[0581] In the present specification, a monovalent non-aromatic condensed polycyclic group refers to a monovalent group in which two or more rings are condensed with each other, and only carbon atoms are included as ring atoms, and the entire molecule has non-aromaticity (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthryl, etc. In the present specification, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0582] In the present specification, a monovalent non-aromatic condensed heteropolycyclic group refers to a monovalent group in which two or more rings are condensed with each other, and at least one heteroatom is included as a ring-forming atom in addition to carbon atoms, and the entire molecule has non-aromatic properties (for example, having 1 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothioyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazoles, The divalent non-aromatic condensed heteropolycyclic group in the present invention refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0583] In this manual, C 6 -C 60 Aryloxy refers to -OA 102 (Among them, A 102 It is the C 6 -C 60 Aryl), the C 6 -C60 Arylthio refers to -SA 103 (Among them, A 103 It is the C 6 -C 60 aryl).

[0584] In this manual, “C 7 -C 60 "Arylalkyl" refers to -A 104 A 105 (Among them, A 104 It is C 1 -C 54 Alkylene, A 105 It is C 6 -C 59 Aryl), in this specification C 2 -C 60 Heteroaralkyl refers to -A 106 A 107 (Among them, A 106 It is C 1 -C 59 Alkylene, A 107 It is C 1 -C 59 heteroaryl).

[0585] In this manual, “R 10a ” can be:

[0586] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;

[0587] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl or C 1 -C 60 Alkoxy;

[0588] Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Aralkyl, C 2 -C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 7 -C 60 Arylalkyl or C 2 -C60 heteroarylalkyl; or

[0589] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0590] In this manual, Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; or deuterated, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group; C 7 -C 60 Arylalkyl or C 2 -C 60 Heteroaralkyl.

[0591] In the present specification, a heteroatom refers to any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0592] In this specification, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, "tert-Bu" or "Bu t” refers to tert-butyl, and “OMe” refers to methoxy.

[0593] In this specification, "biphenyl" refers to "phenyl substituted by phenyl". The "biphenyl" belongs to a group in which the substituent is "C 6 -C 60 "substituted phenyl" or "aryl".

[0594] In this specification, "terphenyl" refers to "phenyl substituted by biphenyl". 6 -C 60 Aryl substituted C 6 -C 60 "substituted phenyl" or "aryl".

[0595] In this specification, the x-axis, y-axis, and z-axis are not limited to the three axes on the rectangular coordinate system, and can be interpreted as including the broad meaning thereof. For example, the x-axis, y-axis, and z-axis can be orthogonal to each other, or can refer to non-orthogonal directions different from each other.

[0596] In the present specification, unless otherwise defined, * and *' mean a binding site between adjacent atoms in the corresponding chemical formula or moiety.

[0597] Hereinafter, the compounds and organic light-emitting elements of an embodiment of the present invention are described in more detail by means of synthesis examples and embodiments. In the following synthesis examples, in the expression "A is replaced by B", the molar equivalent of A and the molar equivalent of B are the same.

[0598] [Synthesis example]

[0599] Synthesis Example 1: Synthesis of Compound 4

[0600]

[0601] (1) Synthesis of intermediate 4-a

[0602] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 21 mmol), N-phenyldibenzo[b,d]furan-4-amine (5.7 g, 21 mmol), pd 2 dba 3(1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 4-a (white solid, 10 g, 75%).

[0603] ESI-LCMS:[M] + :C46H38N2O.634.3031.

[0604] (2) Synthesis of intermediate 4-b

[0605] Under argon atmosphere, intermediate 4-a (10 g, 16 mmol), 1-bromo-3-iodobenzene (4.5 g, 16 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butylphosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 4-b (white solid, 8 g, 64%).

[0606] ESI-LCMS:[M] +:C52H41BrN2O.788.2434.

[0607] (3) Synthesis of intermediate 4-c

[0608] Under argon atmosphere, intermediate 4-b (8 g, 10 mmol), 3-(tert-butyl)-5-chloro-N-phenylaniline (2.6 g, 10 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (2.9 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 4-c (white solid, 7.5 g, 78%).

[0609] ESI-LCMS:[M] + :C68H58ClN3O.967.4234.

[0610] (4) Synthesis of intermediate 4-d

[0611] Under argon atmosphere, intermediate 4-c (7.5 g, 7.7 mmol), N-(3-(9H-carbazol-9-yl-d8)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (3.8 g, 7.7 mmol), pd 2 dba 3(0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (2.9 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 4-d (white solid, 7.8 g, 71%).

[0612] ESI-LCMS:[M] + :C104H75D8N5O.1425.8921.

[0613] (5) Synthesis of Compound 4

[0614] Under argon atmosphere, intermediate 4-d (7.8 g, 5.4 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene (O-DCB), and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 4 (yellow solid, 1.9 g, 24%).

[0615] ESI-LCMS:[M] + :C104H69D8B2N5O.1441.6008

[0616] 1H-NMR (CDCl3): δ=10.22(s,1H),9.66(d,2H),8.20(d,2H),7.98(s,1H),7.64(d,1H) ,7.54(d,1H),7.33(m,13H),7.15(m,12H),7.04(m,17H),6.88(s,1H),1.39(s,18H).

[0617] Synthesis Example 2: Synthesis of Compound 7

[0618]

[0619] (1) Synthesis of intermediate 7-a

[0620] Under argon atmosphere, intermediate 4-b (10 g, 12 mmol), N-(3-(tert-butyl)-5-chlorophenyl)dibenzo[b,d]furan-4-amine (4.5 g, 12 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butylphosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 7-a (white solid, 9.77 g, 77%).

[0621] ESI-LCMS:[M] + :C74H60ClN3O2.1057.4114.

[0622] (2) Synthesis of intermediate 7-b

[0623] Under argon atmosphere, intermediate 7-a (9.77 g, 9.2 mmol), N-(3-(9H-carbazol-9-yl-d8)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (4.5 g, 9.2 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (3 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 7-b (white solid, 9.5 g, 65%).

[0624] ESI-LCMS:[M] + :C110H77D8N5O2.1515.7127.

[0625] (3) Synthesis of Compound 7

[0626] Under argon atmosphere, intermediate 7-b (9.5 g, 6.2 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene (O-DCB), and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 7 (yellow solid, 2 g, 21%).

[0627] ESI-LCMS:[M]+ :C110H71D8B2N5O2.1531.6492

[0628] 1H-NMR (CDCl3): δδ=10.33(s,1H),9.54(d,2H),8.20(d,4H),7.95(s,2H),7.61(d,2H) ),7.51(d,2H),7.41(m,16H),7.13(m,8H),7.08(m,15H),6.84(s,1H),1.42(s,18H).

[0629] Synthesis Example 3: Synthesis of Compound 13

[0630]

[0631] (1) Synthesis of intermediate 13-a

[0632] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 21 mmol), 3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenol (8.2 g, 21 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The intermediate 13-a (white solid, 11.5 g, 74%) was obtained by purification and separation using silica gel column chromatography using hexane as a developing solvent. ESI-LCMS: [M] + :C54H54N2O.746.4120.

[0633] (2) Synthesis of intermediate 13-b

[0634] Under argon atmosphere, intermediate 13-a (11.5 g, 15 mmol), 1-bromo-3-iodobenzene (4.3 g, 15 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 13-b (white solid, 9.5 g, 70%).

[0635] ESI-LCMS:[M] + :C60H57BrN2O.900.3711.

[0636] (3) Synthesis of intermediate 13-c

[0637] Under argon atmosphere, intermediate 13-b (9.5 g, 10 mmol), N-(3-(tert-butyl)-5-chlorophenyl)dibenzo[b,d]furan-4-amine (3.7 g, 10 mmol), pd 2 dba 3(0.9 g, 1 mmol), tris-tert-butylphosphine (1 mL, 2 mmol), sodium tert-butoxide (2.9 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 13-c (white solid, 8.6 g, 74%).

[0638] ESI-LCMS:[M] + :C82H76ClN3O2.1169.5612.

[0639] (4) Synthesis of intermediate 13-d

[0640] Under argon atmosphere, intermediate 13-c (8.6 g, 7.3 mmol), N-phenyl-[1,1':3',1"-terphenyl]-2'-amine (2.3 g, 7.3 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (2.9 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 13-d (white solid, 6.9 g, 65%).

[0641] ESI-LCMS:[M] + :C106H94N4O2.1454.7434.

[0642] (5) Synthesis of Compound 13

[0643] Under argon atmosphere, intermediate 13-d (6.9 g, 4.7 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene (O-DCB), and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 13 (yellow solid, 1.6 g, 23%).

[0644] ESI-LCMS:[M] + :C106H88B2N4O2.1470.7041

[0645] 1H-NMR (CDCl3): δδ=10.25(s,1H),9.52(d,2H),8.95(s,2H),8.20(d,4H),7.95(d,1H),7.86(d,2H),7.62 (m,3H),7.51(m,5H),7.39(m,14H),7.10(m,16H),6.88(s,1H),6.70(s,1H),1.44(s,18H),1.39(s,18H).

[0646] Synthesis Example 4: Synthesis of Compound 34

[0647]

[0648] (1) Synthesis of Intermediate 34-a

[0649] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 21 mmol), N-(3-chlorophenyl)dibenzo[b,d]furan-4-amine (6.4 g, 21 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butylphosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 34-a (white solid, 10 g, 71%).

[0650] ESI-LCMS:[M] + :C46H37ClN2O.668.2614.

[0651] (2) Synthesis of intermediate 34-b

[0652] In a 2L flask under argon atmosphere, intermediate 34-a (10 g, 15 mmol), 3-phenyl-9H-carbazole (3.6 g, 15 mmol), pd 2 dba 3(1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 34-b (white solid, 9.7 g, 74%).

[0653] ESI-LCMS:[M] + :C64H49N3O.875.3009.

[0654] (3) Synthesis of intermediate 34-c

[0655] Under argon atmosphere, intermediate 34-b (10 g, 11 mmol), 3-iodophenol (2.4 g, 11 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butylphosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 34-c (white solid, 6.7 g, 73%).

[0656] ESI-LCMS:[M] +:C70H53N3O2.967.4137.

[0657] (4) Synthesis of intermediate 34-d

[0658] Under argon atmosphere, intermediate 34-c (6.7 g, 7 mmol), 1,3-dibromo-5-(tert-butyl)benzene (2 g, 7 mmol), CuI (1.3 g, 7 mmol), K 2 CO 3 (2.9 g, 21 mmol), 1,10-phenanthroline (0.9 g, 7 mmol), and dissolved in 100 mL of N,N-dimethylformamide (DMF), and then the reaction solution was stirred at 120°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 34-d (white solid, 5.7 g, 60%).

[0659] ESI-LCMS:[M] + :C80H64BrN3O2.1177.4241.

[0660] (5) Synthesis of intermediate 34-e

[0661] Under argon atmosphere, a 2L flask was charged with intermediate 34-d (5.7 g, 4.8 mmol), N-(3-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (1.8 g, 4.8 mmol), pd 2 dba 3(0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 34-e (white solid, 5.1 g, 75%).

[0662] ESI-LCMS:[M] + :C108H90N4O2.1474.7017.

[0663] (6) Synthesis of Compound 34

[0664] Under argon atmosphere, intermediate 34-e (5 g, 3.3 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene (O-DCB), and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 34 (yellow solid, 1.2 g, 25%).

[0665] ESI-LCMS:[M] + :C108H84B2N4O2.1490.6127

[0666] 1H-NMR (CDCl3): δ=10.21(s,1H),9.67(d,2H),8.55(d,1H),8.22(d,4H),7.94(m,4H),7.78(m,3H),7.45 (m,14H),7.28(m,10H),7.08(m,12H),6.99(d,1H),6.83(s,1H),6.70(s,1H),1.32(s,18H),1.05(s,9H).

[0667] Synthesis Example 5: Synthesis of Compound 53

[0668]

[0669] (1) Synthesis of Intermediate 53-a

[0670] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 21 mmol), N-(3-chlorophenyl)dibenzo[b,d]furan-4-amine (6.4 g, 21 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butylphosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 53-a (white solid, 10 g, 71%).

[0671] ESI-LCMS:[M] + :C46H37ClN2O.668.2614.

[0672] (2) Synthesis of Intermediate 53-b

[0673] In a 2L flask under argon atmosphere, intermediate 53-a (10 g, 15 mmol), 9H-carbazole (3.6 g, 15 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butylphosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 53-b (white solid, 8.5 g, 71%).

[0674] ESI-LCMS:[M] + :C58H45N3O.799.3626.

[0675] (3) Synthesis of Intermediate 53-c

[0676] Under argon atmosphere, intermediate 53-b (8.5 g, 10 mmol), 1-bromo-3-iodobenzene (3 g, 11 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butylphosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 53-c (white solid, 6.2 g, 65%).

[0677] ESI-LCMS:[M] + :C64H48BrN3O.953.0023.

[0678] (4) Synthesis of Intermediate 53-d

[0679] Under argon atmosphere, intermediate 53-c (6.2 g, 6.5 mmol), N-(3-(tert-butyl)-5-chlorophenyl)dibenzo[b,d]furan-4-amine (2.3 g, 6.5 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butylphosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 53-d (white solid, 6 g, 74%).

[0680] ESI-LCMS:[M] + :C86H67ClN4O2.1222.5127.

[0681] (5) Synthesis of Intermediate 53-e

[0682] Under argon atmosphere, intermediate 53-d (6 g, 4.9 mmol), N-(3-(9H-carbazol-9-yl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (2.4 g, 4.9 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 53-e (white solid, 6.3 g, 77%).

[0683] ESI-LCMS:[M] + :C122H92N6O2.1672.7311.

[0684] (6) Synthesis of Compound 53

[0685] Under argon atmosphere, intermediate 53-e (6.3 g, 3.7 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene (O-DCB), and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 53 (yellow solid, 1.4 g, 22%).

[0686] ESI-LCMS:[M] +:C122H86B2N6O2.1688.7747

[0687] 1H-NMR (CDCl3): δδδ=10.24(s,1H),9.61(d,2H),8.51(d,4H),7.92(m,6H),7.48(m,12 H),7.35(m,11H),7.20(m,12H),7.08(m,10H),6.97(d,2H),6.85(s,1H)1.32(s,18H).

[0688] Synthesis Example 6: Synthesis of Compound 78

[0689]

[0690] (1) Synthesis of intermediate 78-a

[0691] Under argon atmosphere, N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (10 g, 22 mmol), 3-iodophenol (4.8 g, 21 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 78-a (white solid, 7.5 g, 62%).

[0692] ESI-LCMS:[M] + :C34H30BrNO.547.1512.

[0693] (2) Synthesis of intermediate 78-b

[0694] Under argon atmosphere, intermediate 78-a (10 g, 13.7 mmol), N-(3-(9H-carbazol-9-yl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (6.7 g, 13.7 mmol), pd 2 dba 3 (1.6 g, 1.9 mmol), tris-tert-butyl phosphine (1.6 mL, 3.8 mmol), sodium tert-butoxide (11.5 g, 120 mmol), and dissolved in 300 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 78-b (white solid, 9.5 g, 73%).

[0695] ESI-LCMS:[M] + :C70H55N3O.953.4323.

[0696] (3) Synthesis of intermediate 78-c

[0697] Under argon atmosphere, intermediate 78-b (9.5 g, 10 mmol), 1,3-dibromo-5-(tert-butyl)benzene (2.9 g, 10 mmol), CuI (1.9 g, 10 mmol), K 2 CO 3(4.2 g, 30 mmol), 1,10-phenanthroline (1.3 g, 10 mmol), and dissolved in 100 mL of N,N-dimethylformamide (DMF), and then the reaction solution was stirred at 120°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The residue was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 78-c (white solid, 7.6 g, 65%).

[0698] ESI-LCMS:[M] + :C80H63BBrN3O.1171.4234.

[0699] (4) Synthesis of intermediate 78-d

[0700] Under argon atmosphere, intermediate 78-c (7.6 g, 6.5 mmol), N,2-diphenyldibenzo[b,d]furan-4-amine (2.1 g, 6.5 mmol), pd 2 dba 3 (0.9 g, 1 mmol), tris-tert-butyl phosphine (1 mL, 2 mmol), sodium tert-butoxide (3.0 g, 30 mmol), and dissolved in 100 mL of xylene, and then the reaction solution was stirred at 140 ° C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction and the organic layer was collected, and then MgSO 4 After drying, the mixture was filtered. The filtered solution was decompressed to remove the solvent, and the obtained solid was purified by CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Intermediate 78-d (white solid, 6.7 g, 73%).

[0701] ESI-LCMS:[M] +:C104H82N4O2.1418.6004.

[0702] (5) Synthesis of Compound 78

[0703] Under argon atmosphere, intermediate 78-d (6.7 g, 4.7 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and then BBr was added. 3 (1.5 equivalents). The reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine was added to terminate the reaction, the pressure was reduced to remove the solvent, and the obtained solid was separated by using CH 2 Cl 2 The product was purified and separated by column chromatography using silica gel and hexane as a developing solvent to obtain Compound 78 (yellow solid, 1.24 g, 22%).

[0704] ESI-LCMS:[M] + :C104H76B2N4O2.1434.6127

[0705] 1H-NMR (CDCl3): δ=10.29(s,1H),9.54(d,2H),8.55(d,2H),8.26(s,1H),8.19(m,5H),7.95(m,2H),7.75 (m,2H),7.50(s,1H),7.43(m,15H),7.31(m,10H),7.16(m,12H),6.95(s,1H),6.70(s,1H),1.38(s,18H).

[0706] [Example]

[0707] Example 1

[0708] Will form a 15Ω / cm 2 The glass substrate (Corning product) with an ITO electrode as the first electrode was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes respectively, irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and then installed in a vacuum deposition device.

[0709] The NPD is formed by depositing NPD on the first electrode. After a hole injection layer of a thickness of 1000 mm, H-1-19 is deposited on the hole injection layer to form Then, CzSi is deposited on the hole transport layer to form a hole transport layer having a thickness of The thickness of the electron blocking layer is

[0710] The electron blocking layer is formed by co-depositing a host compound having a first host HT1 and a second host ET1 mixed in a ratio of 1:1, a photosensitive agent (PS1), and a compound 4 in a weight ratio of 85:14:1 on the upper side of the electron blocking layer. Thickness of the luminous layer.

[0711] Next, TSPO1 is deposited on the light-emitting layer to form After a hole blocking layer of a thickness of 1000 mm, TPBi is deposited on the hole blocking layer to form a The electron transport layer is formed by depositing LiF on the electron transport layer. The thickness of the electron injection layer.

[0712] The electron injection layer is formed by depositing Al on the electron injection layer. A second electrode having a thickness of 1000 mm is formed by depositing CP4 on the upper portion of the electrode. A covering layer of thickness is formed to produce an organic electroluminescent element.

[0713] The following discloses compounds for use in producing an organic electroluminescent element.

[0714]

[0715] Examples 2 to 6 and Comparative Examples 1 to 5

[0716] An organic light-emitting element was manufactured in the same manner as in Example 1 except that the compound listed in Table 2 below was used as a dopant when forming the light-emitting layer.

[0717] [Evaluation example]

[0718] Evaluation Example 1: Evaluation of physical properties of compounds

[0719] The E of the compounds synthesized according to Synthesis Examples 1 to 6 and the compounds used in Comparative Examples HOMO The measurements were performed using the Smart Manager software of the SP2 electrochemical workstation from ZIVELAB.

[0720] The λ values ​​of the compounds synthesized according to Synthesis Examples 1 to 6 and the compounds used in Comparative Examples were measured using Labsolution UV-Vis software using a UV-1800 UV / Visible Scanning Spectrophotometer manufactured by Shimadzu Corporation equipped with a deuterium / tungsten-halogen light source and a silicon photodiode. Abs Measurements were taken.

[0721] The λ values ​​of the compounds synthesized in Synthesis Examples 1 to 6 and the compounds used in Comparative Examples were measured using FluorEssence software on a fluoromax+spectrometer equipped with a xenon light source and a monochromator. emi Measurements were taken.

[0722] Stokes shift refers to the difference between the maximum wavelength when absorbing energy and the maximum wavelength when releasing energy.

[0723] [Table 1]

[0724]

[0725]

[0726]

[0727] From the above Table 1, it is confirmed that the compounds of the present invention have shorter or equivalent maximum emission wavelengths and lower highest occupied molecular orbital energies (E) than those of the comparative examples A to E. HOMO ).

[0728] Evaluation Example 2: Evaluation of Characteristics of Organic Light Emitting Elements

[0729] The organic light emitting elements manufactured in Examples 1 to 6 and Comparative Examples 1 to 5 were measured at 1000 cd / m by using Keithley MU 236 and luminance meter PR650. 2 The driving voltage, top luminous efficiency, maximum luminous wavelength, and lifetime (T 95 ) and CIE y The values ​​were measured and the results are shown in Table 2.

[0730] The top emission efficiency indicates the emission efficiency of a top emission type light emitting element, and CIE(x,y) indicates the CIE color coordinates. 95 ) is a result obtained by measuring the time taken for the luminance to decrease to 95% relative to the initial luminance and calculating the relative lifespan based on Comparative Example 1.

[0731] [Table 2]

[0732]

[0733] From the above Table 2, it is confirmed that the organic light-emitting elements of Examples 1 to 6 have shorter or equal emission wavelengths, higher top emission efficiencies, and significantly superior lifespans compared to the organic light-emitting elements of Comparative Examples 1 to 5.

[0734] In Comparative Examples 1 to 5 using Compounds A to E having HOMO levels higher than -5.3 eV, the lifetime is extremely short because excitons are directly formed in the dopant by a direct trap-assistant recombination mechanism.

[0735] In addition, Comparative Examples 1 to 4 using Compound A to Compound D whose emission wavelengths deviate from the deep blue emission wavelength have the characteristics that the efficiency is greatly reduced and the lifetime is shortened in the top emission element.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: <Chemical Formula 2> <Chemical formula 3> In the chemical formula 1, the chemical formula 2 and the chemical formula 3, Ar1, Ar2, Ar3, Ar4, Ar5, Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 ,Ar 31 ,Ar 32 ,Ar 41 and Ar 42 Independently of each other, C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, T1, T2, T3 and T4 are independently N(Y2), N(Y3), N(R6), P(R6), C(R7)(R8), Si(R7)(R8), O, S or Se, Y2 is a group represented by the chemical formula 2, Y3 is a group represented by the chemical formula 3, a1 and a2 are independently 0, 1 or 2, The sum of a1 and a2 is greater than 1, T 41 is O or S, * is the binding site with the adjacent nitrogen atom, X3, X4, R1, R2, R3, R4, R5, R6, R7, R8, Z1, Z2, Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z4 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazine, and at least one R 10a Substituted or unsubstituted C1-C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C1-C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C1-C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C3-C 10 Cycloalkenyl, with at least one R 10a Substituted or unsubstituted C1-C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryl, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C6-C 60 Arylthio, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroaryl, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroaryloxy, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroarylthio, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2), X3, X4, R1, R2, R3, R4, R5, R6, R7, Z1, Z2, Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z4 can selectively combine with each other to form at least one R 10a Substituted or unsubstituted C5-C 60 A carbocyclic group or a 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups, n1, n2, n3, n4 and n5 are each independently an integer from 0 to 10, m1, m2, m31, m32 and m4 are independently integers from 0 to 15, The R 10a for, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy; Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 arylthio; or Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) Or P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To the Q 13 Q 21 To the Q 23 And the Q 31 To the Q 33 independently of each other are hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.

2. The heterocyclic compound according to claim 1, wherein The heterocyclic compound represented by the chemical formula 1 is a compound represented by the following chemical formula 1-1: <Chemical Formula 1-1> In the chemical formula 1-1, For Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 , T1, T2, T3, T4, a1, a2, X3, X4, R1, R2, Z1, Z2, n1, n2, m1 and m2, refer to claim 1, For R 31 and R 32 The description of R3 in claim 1 is independently referred to. For R 41 and R 42 The description of R4 in claim 1 is independently referred to. For R 51 and R 52 The description of R5 in claim 1 is independent of each other.

3. The heterocyclic compound according to claim 1, wherein T1, T2, T3 and T4 are independently N(Y2), N(Y3), N(R6), O, S or Se.

4. The heterocyclic compound according to claim 1, wherein At least one of T1, T2, T3, and T4 is N(Y2).

5. The heterocyclic compound according to claim 1, wherein At least one of T1, T2, T3, and T4 is N(Y3).

6. The heterocyclic compound according to claim 1, wherein Satisfy any one of the following conditions i) to iii): i) a1 is 1, a2 is 0; ii) a1 is 0 and a2 is 1; or iii) a1 and a2 are both 1.

7. The heterocyclic compound according to claim 1, wherein The heterocyclic compound represented by the chemical formula 1 is a compound represented by any one of the following chemical formulas 1-21 to 1-23: <Chemical Formula 1-21> <Chemical Formula 1-22> <Chemical Formula 1-23> In the chemical formula 1-21, the chemical formula 1-22 and the chemical formula 1-23, For Ar3, Ar4, Ar5, Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 , T1, T2, T3, T4, X3, X4, R3, R4, R5, Z1, Z2, n3, n4, n5, m1 and m2 The content described in claim 1, For R 11 , R 12 , R 13 and R 14 The description of R1 in claim 1 is independent of each other. For R 21 , R 22 , R 23 and R 24 The description of R2 in claim 1 is independent of each other.

8. The heterocyclic compound according to claim 1, wherein By the The group represented by the following chemical formula 1A is represented by The group represented by is a group represented by the following chemical formula 1B: <Chemical Formula 1A> <Chemical Formula 1B> In the chemical formula 1A and the chemical formula 1B, For Z 11 To Z 18 The description of Z1 in claim 1 is independent of each other. For Z 21 To Z 28 The description of Z2 in claim 1 is independent of each other, and *' is a binding site with an adjacent atom.

9. The heterocyclic compound according to claim 1, wherein The group represented by the chemical formula 2 is a group represented by the following chemical formula 2-1: <Chemical Formula 2-1> In the chemical formula 2-1, For Z 3A To Z 3C The description of the invention refers to the contents described in claim 1. For Z 3D To Z 3H The description of Z in claim 1 is independent of each other. 31 Description, For Z 3I To Z 3M The description of Z in claim 1 is independent of each other. 32 Description, * indicates the binding site with the adjacent nitrogen atom.

10. The heterocyclic compound according to claim 1, wherein The group represented by the chemical formula 3 is a group represented by any one of the following chemical formulas 3-1 to 3-4: <Chemical Formula 3-1> <Chemical Formula 3-2> <Chemical Formula 3-3> <Chemical Formula 3-4> In the chemical formula 3-1 to the chemical formula 3-4, For T 41 The description of the invention refers to the description in claim 1. For Z 41 To Z 48 The description of Z4 in claim 1 is independent of each other. * is the binding site with the adjacent nitrogen atom.

11. The heterocyclic compound according to claim 1, wherein R6 is at least one R 10a Substituted or unsubstituted C6-C 20 Aryl or at least one R 10a Substituted or unsubstituted C1-C 20 Heteroaryl.

12. The heterocyclic compound according to claim 1, wherein The heterocyclic compound represented by the chemical formula 1 is selected from one of the following compounds 1 to 80:

13. An organic light emitting element, comprising: a first electrode; a second electrode, facing the first electrode; as well as An intermediate layer, comprising a light-emitting layer sandwiched between the first electrode and the second electrode, wherein the organic light-emitting element comprises a heterocyclic compound represented by the following chemical formula 1: <Chemical Formula 2> <Chemical formula 3> In the chemical formula 1, the chemical formula 2 and the chemical formula 3, Ar1, Ar2, Ar3, Ar4, Ar5, Ar 11 ,Ar 12 ,Ar 21 ,Ar 22 ,Ar 31 ,Ar 32 ,Ar 41 and Ar 42 Independently of each other, C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, T1, T2, T3 and T4 are independently N(Y2), N(Y3), N(R6), P(R6), C(R7)(R8), Si(R7)(R8), O, S or Se, Y2 is a group represented by the chemical formula 2, Y3 is a group represented by the chemical formula 3, a1 and a2 are independently 0, 1 or 2, The sum of a1 and a2 is greater than 1, T 41 is O or S, * is the binding site with the adjacent nitrogen atom, X3, X4, R1, R2, R3, R4, R5, R6, R7, R8, Z1, Z2, Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z4 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazine, and at least one R 10a Substituted or unsubstituted C1-C 60 Alkyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkenyl, with at least one R 10a Substituted or unsubstituted C2-C 60 Alkynyl, with at least one R 10a Substituted or unsubstituted C1-C 60 Alkoxy, with at least one R 10a Substituted or unsubstituted C3-C 10 Cycloalkyl, with at least one R 10a Substituted or unsubstituted C1-C 10 Heterocycloalkyl, with at least one R 10a Substituted or unsubstituted C3-C 10 Cycloalkenyl, with at least one R 10a Substituted or unsubstituted C1-C 10 Heterocycloalkenyl, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryl, with at least one R 10a Substituted or unsubstituted C6-C 60 Aryloxy, with at least one R 10a Substituted or unsubstituted C6-C 60 Arylthio, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroaryl, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroaryloxy, with at least one R 10a Substituted or unsubstituted C1-C 60 Heteroarylthio, with at least one R 10a A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted by at least one R 10a a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2), X3, X4, R1, R2, R3, R4, R5, R6, R7, Z1, Z2, Z 3A , Z 3B , Z 3C , Z 31 , Z 32 and Z4 can selectively combine with each other to form at least one R 10a Substituted or unsubstituted C5-C 60 A carbocyclic group or a 10a Substituted or unsubstituted C1-C 60 Heterocyclic groups, n1, n2, n3, n4 and n5 are each independently an integer from 0 to 10, m1, m2, m31, m32 and m4 are independently integers from 0 to 15, The R 10a for, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro; Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted or unsubstituted C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy; Deuterated, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio; or Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) Or P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To the Q 13 Q 21 To the Q 23 And the Q 31 To the Q 33 independently of each other are hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkynyl; C1-C 60 Alkoxy; or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, phenyl, biphenyl or any combination thereof substituted or unsubstituted C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.

14. The organic light emitting element according to claim 13, wherein: The first electrode is an anode, The second electrode is a cathode, The intermediate layer further includes a hole transport region arranged between the first electrode and the light emitting layer and an electron transport region arranged between the light emitting layer and the second electrode, The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, a buffer layer, a light-emitting auxiliary layer, and an electron blocking layer. The electron transport region includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

15. The organic light emitting element according to claim 13, wherein: The light emitting layer includes the heterocyclic compound.

16. The organic light emitting element according to claim 13, wherein: The light-emitting layer includes a host and a dopant, The dopant includes the heterocyclic compound.

17. The organic light emitting element according to claim 13, wherein: The light-emitting layer also includes a photosensitizer. 18 . An electronic device comprising the organic light emitting element according to claim 13 .

19. The electronic device as claimed in claim 18, further comprising a thin film transistor, The thin film transistor includes a source electrode and a drain electrode, The first electrode of the organic light emitting element is electrically connected to at least one of the source electrode and the drain electrode of the thin film transistor.

20. A consumer product comprising the organic light emitting element according to any one of claims 13 to 17.

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