Organic electroluminescent compound, organic electroluminescent material comprising same, and organic electroluminescent device

Abstract

The invention relates to an organic electroluminescent compound, an organic electroluminescent material comprising the same, and an organic electroluminescent device. Provided is an organic electroluminescent compound represented by the following Formula 2.

Description

[0001] This invention patent application is a divisional application of the invention patent application with application number 202110289682.2, application date March 15, 2021, entitled "Organic electroluminescent compound, organic electroluminescent material comprising the same, and organic electroluminescent device". Technical Field

[0002] This disclosure relates to an organic electroluminescent compound, an organic electroluminescent material comprising the same, and an organic electroluminescent device. Background Technology

[0003] Among display devices, electroluminescent devices (EL devices) are a type of self-emissive display device, which has the advantages of providing a wider viewing angle, a higher contrast ratio, and a faster response time. Organic EL devices were first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0004] Organic light-emitting diodes (OLEDs) consist of a multilayer structure to improve their efficiency and stability. This multilayer structure includes a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In this context, selecting compounds contained in the hole transport layer, etc., is considered one means of improving device characteristics such as hole transport efficiency to the emissive layer, luminous efficiency, and lifetime.

[0005] In this regard, compounds such as copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), and 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (MTDATA) are used as hole injection and transport materials in OLEDs. However, OLEDs prepared using these materials suffer from reduced quantum efficiency and lifetime. This is due to thermal stress occurring between the anode and the hole injection layer when the OLED is driven at high currents, which significantly reduces the device lifetime. Furthermore, the very high hole mobility of the organic materials used in the hole injection layer leads to a disruption of the hole-electron charge balance and a decrease in quantum efficiency (cd / A).

[0006] Therefore, there is still a need to develop hole transport layer materials to improve OLED performance.

[0007] U.S. Patent No. 8,343,637B2 discloses a compound in which tetramethylphenanthrene is used as a linker in a carbazole-carbazole compound, serving as an example of a host material. However, the reference does not disclose specific apparatus examples or methods for synthesizing the compound. Furthermore, the compound in the reference is not used as a material for a hole transport layer. Summary of the Invention

[0008] Technical issues

[0009] The purpose of this disclosure is firstly to provide an organic electroluminescent compound that can be used to prepare an organic electroluminescent device having a low driving voltage and / or high luminous efficiency and / or long lifetime, and secondly, to provide an organic electroluminescent device comprising the organic electroluminescent compound.

[0010] Solution to the problem

[0011] As a result of in-depth research to solve the above-mentioned technical problems, the inventors of this invention discovered that compounds having a dihydrophenanthrene moiety, represented by Formula 1 below, have improved degradation properties, thus completing this invention.

[0012]

[0013] In Equation 1,

[0014] R1 to R4 each independently represent *-(L1) a -(Ar1) b Hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings;

[0015] R5 to R 12 Each can be represented independently as *-(L1) a -(Ar1) bHydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl; or may be attached to one or more adjacent substituents to form one or more rings;

[0016] The premise is R1 to R 12 At least one of the following represents *-(L1) a -(Ar1) b ;

[0017] L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0018] Ar1 represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -N-(Ar2)(Ar3);

[0019] Ar2 and Ar3 each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C3-C30) aliphatic rings and (C6-C30) aromatic rings fused rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0020] a represents an integer of 1 or 2, and b represents an integer from 1 to 4; and when a and b are 2 or greater, each L1 and each Ar1 can be the same or different;

[0021] The premise is that compounds having Formula 1 are excluded, where R5 to R... 10 and R 12 It is hydrogen, and R 11 Including substituted amino groups.

[0022] Beneficial effects of the present invention

[0023] Organic electroluminescent devices having low driving voltage and / or high luminous efficiency and / or long lifetime can be manufactured by comprising an organic electroluminescent compound according to the present disclosure and an organic electroluminescent material comprising the organic electroluminescent compound. Detailed Implementation

[0024] This disclosure will now be described in detail. However, the following description is intended to explain the invention and is not intended to limit the scope of the invention in any way.

[0025] This disclosure relates to an organic electroluminescent compound represented by Formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent material.

[0026] Furthermore, this disclosure relates to an organic electroluminescent compound represented by Formula 2 and an organic electroluminescent device comprising said organic electroluminescent compound.

[0027] Furthermore, this disclosure relates to an organic electroluminescent compound represented by Formula 3 and an organic electroluminescent device comprising said organic electroluminescent compound.

[0028] The term "organic electroluminescent compound" in this disclosure means a compound that can be used in an organic electroluminescent device and can be included, as needed, in any layer constituting the organic electroluminescent device.

[0029] The term "organic electroluminescent material" in this disclosure refers to a material that can be used in an organic electroluminescent device and may contain at least one compound. If desired, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including host material and dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0030] The term "multiple host materials" in this disclosure refers to an organic electroluminescent material comprising a combination of at least two host materials. It can mean both a material before being included in an organic electroluminescent device (e.g., before vapor deposition) and a material after being included in the organic electroluminescent device (e.g., after vapor deposition). The multiple host materials of this disclosure can be included in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds included in the multiple host materials of this disclosure can be included in one light-emitting layer, or they can be included in different light-emitting layers. When at least two host materials are included in one layer, the at least two host materials can be mixed and evaporated to form the layer, or they can be co-evaporated separately and simultaneously to form the layer.

[0031] In this disclosure, the term "(C1-C30)alkyl" refers to a straight-chain or branched alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The aforementioned alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. In this disclosure, the term "(C2-C30)alkenyl" refers to a straight-chain or branched alkenyl group having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The aforementioned alkenyl group may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. In this disclosure, the term "(C3-C30)cycloalkyl" refers to a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms in its cyclic skeleton, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The aforementioned cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, etc. In this disclosure, the term "(3- to 7-membered) heterocycloalkyl" refers to a cycloalkyl having 3 to 7 cyclic skeleton atoms, preferably 5 to 7 cyclic skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, etc. In this disclosure, the term "(C6-C30)(aryl)" refers to a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 carbon atoms in its ring skeleton, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15, and may be partially saturated, and may include a spirostructure. Examples of aryl groups specifically include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, binatyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[a]fluorenyl, diphenylbenzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthrene, benzo[a]phenanthrene, phenylphenanthrene, anthracene, benzo[a]anthrene, indene, triphenylene, pyrene, tetraphenyl, perylene, etc. Benzyl, benzo[ It includes alkyl, naphthyl, fluoranthyl, benzofluoranthyl, tolyl, xylyl, trimethylyl, cumenel, spiro[fluorene-fluorene]yl, spiro[fluorene-benzofluorene]yl, azulel, tetramethyl-dihydrophenanthrene, etc. More specifically, the aryl group can be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylelel, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4'-tert-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl 1-Naphthyl, p-terphenyl-2-yl, m-tetraphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 1-phenanthyl, 2-phenanthyl, 3-phenanthyl, 4-phenanthyl, 9-phenanthyl, 1- basal, 2- basal, 3- basal, 4- Base, 5- Base, 6- Benzyl, benzo[c]phenanthrene, benzo[g] 1-Triphenylene, 2-Triphenylene, 3-Triphenylene, 4-Triphenylene, 3-Fluoranthryl, 4-Fluoranthryl, 8-Fluoranthryl, 9-Fluoranthryl, benzo[a]fluorenyl, 11,11-Dimethyl-1-benzo[a]fluorenyl, 11,11-Dimethyl-2-benzo[a]fluorenyl, 11,11-Dimethyl-3-benzo[a]fluorenyl, 11, 11-Dimethyl-4-benzo[a]fluorenyl, 11,11-dimethyl-5-benzo[a]fluorenyl, 11,11-dimethyl-6-benzo[a]fluorenyl, 11,11-dimethyl-7-benzo[a]fluorenyl, 11,11-dimethyl-8-benzo[a]fluorenyl, 11,11-dimethyl-9-benzo[a]fluorenyl, 11,11- Dimethyl-10-benzo[a]fluorenyl, 11,11-dimethyl-1-benzo[b]fluorenyl, 11,11-dimethyl-2-benzo[b]fluorenyl, 11,11-dimethyl-3-benzo[b]fluorenyl, 11,11-dimethyl-4-benzo[b]fluorenyl, 11,11-dimethyl-5-benzo[b]fluorenyl, 11,11-dimethyl 11,11-Dimethyl-7-benzo[b]fluorenyl, 11,11-Dimethyl-8-benzo[b]fluorenyl, 11,11-Dimethyl-9-benzo[b]fluorenyl, 11,11-Dimethyl-10-benzo[b]fluorenyl, 11,11-Dimethyl-1-benzo[c]fluorenyl, 11,11-Dimethyl-2 -Benzo[c]fluorenyl, 11,11-dimethyl-3-benzo[c]fluorenyl, 11,11-dimethyl-4-benzo[c]fluorenyl, 11,11-dimethyl-5-benzo[c]fluorenyl, 11,11-dimethyl-6-benzo[c]fluorenyl, 11,11-dimethyl-7-benzo[c]fluorenyl, 11,11-dimethyl-8-benzo[c]fluorenyl [c]fluorenyl, 11,11-dimethyl-9-benzo[c]fluorenyl, 11,11-dimethyl-10-benzo[c]fluorenyl, 11,11-diphenyl-1-benzo[a]fluorenyl, 11,11-diphenyl-2-benzo[a]fluorenyl, 11,11-diphenyl-3-benzo[a]fluorenyl, 11,11-diphenyl-4-benzo[a] Fluorenyl, 11,11-diphenyl-5-benzo[a]fluorenyl, 11,11-diphenyl-6-benzo[a]fluorenyl, 11,11-diphenyl-7-benzo[a]fluorenyl, 11,11-diphenyl-8-benzo[a]fluorenyl, 11,11-diphenyl-9-benzo[a]fluorenyl, 11,11-diphenyl-10-benzo[a]fluorenyl 11,11-diphenyl-1-benzo[b]fluorenyl, 11,11-diphenyl-2-benzo[b]fluorenyl, 11,11-diphenyl-3-benzo[b]fluorenyl, 11,11-diphenyl-4-benzo[b]fluorenyl, 11,11-diphenyl-5-benzo[b]fluorenyl, 11,11-diphenyl-6-benzo[b]fluorenyl, 11,11-Diphenyl-7-benzo[b]fluorenyl, 11,11-diphenyl-8-benzo[b]fluorenyl, 11,11-diphenyl-9-benzo[b]fluorenyl, 11,11-diphenyl-10-benzo[b]fluorenyl, 11,11-diphenyl-1-benzo[c]fluorenyl, 11,11-diphenyl-2-benzo[c]fluorenyl, 11,11-diphenyl-3-benzo[c]fluorenyl, 11,11-diphenyl-4-benzo[c]fluorenyl, 11,11-diphenyl-5-benzo[c]fluorenyl, 11,11-diphenyl- 6-Benzo[c]fluorenyl, 11,11-diphenyl-7-benzo[c]fluorenyl, 11,11-diphenyl-8-benzo[c]fluorenyl, 11,11-diphenyl-9-benzo[c]fluorenyl, 11,11-diphenyl-10-benzo[c]fluorenyl, 9,9,10,10-tetramethyl-9,10-dihydro-1-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-2-phenanthyl, 9,9,10,10-tetramethyl-9,10-dihydro-3-phenanthyl, 9,9,10,10-tetramethyl-9,10-Dihydro-4-phenanthrene, etc. In this disclosure, the term "(3 to 30-membered) (hybrid)aryl" is an aryl group having 3 to 30 ring skeleton atoms, said ring skeleton atoms including at least one heteroatom selected from the group consisting of B, N, O, S, Si, P, Se, and Ge, preferably at least one heteroatom selected from N, O, and S, wherein the number of ring skeleton carbon atoms is preferably 5 to 25. The number of heteroatoms in the heteroaryl group is preferably 1 to 4. The aforementioned heteroaryl group can be a monocyclic ring or a fused ring condensed with at least one benzene ring; and can be partially saturated. Furthermore, in this document, the aforementioned heteroaryl group can be a heteroaryl group formed by attaching at least one heteroaryl group or aryl group to a heteroaryl group via one or more single bonds. Specific examples of heteroaryl groups can include monocyclic heteroaryl groups, including furanyl, thiopheneyl, pyrroleyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetraazinyl, triazolyl, tetraazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and fused-ring heteroaryl groups, including benzofuranyl, benzothiopheneyl, isobenzofuranyl, dibenzofuranyl, etc. Benzyl, dibenzothiophene, dibenzoselenophene, benzofuranoquinolinyl, benzofuranoquinazolinyl, benzofuranonaphthidyl, benzofuranopyrimidyl, naphthofuranopyrimidyl, benzothiophenequinolinyl, benzothiophenequinazolinyl, benzothiophene naphthophenidyl, benzothiophene pyrimidyl, naphthophene pyrimidyl, pyrimidylindolyl, benzopyrimidylindolyl, benzofuranopyrazinyl, naphthofurano Pyrazinyl, benzothiophene-pyrazinyl, naphthothiophene-pyrazinyl, pyrazinodolyl, benzopyrazinodolyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisooxazolyl, benzooxazolyl, imidazopyridyl, isoindodolyl, indodolyl, benzoindodolyl, indazoleyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxalolinyl, carbazoleyl, azacarbazoleyl, benzocarbazoleyl Azolyl, dibenzocarbazoyl, phenoxazinyl, phenanthidyl, benzodioxanepentenyl, indololinyl, acridineyl, silafluorenyl, germanfluorenyl, benzotriazolyl, phenazinyl, imidazopyridyl, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylbenzopyrimidinyl, indolocarbazoyl, indenecarbazoyl, etc. More specifically, heteroaryl groups can be 1-pyrrolithyl, 2-pyrrolithyl, 3-pyrrolithyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-Triazine-2-yl, 1-Imidazolyl, 2-Imidazolyl, 1-Pyrazolyl, 1-Indolithidyl, 2-Indolithidyl, 3-Indolithidyl, 5-Indolithidyl, 6-Indolithidyl, 7-Indolithidyl, 8-Indolithidyl, 2-Imidazolopyridyl, 3-Imidazolopyridyl, 5-Imidazolopyridyl, 6-Imidazolopyridyl 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furfuryl, 3-Furfuryl, 2- Benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl 6-Quinolinyl, 7-Quinolinyl, 8-Quinolinyl, 1-Isoquinolinyl, 3-Isoquinolinyl, 4-Isoquinolinyl, 5-Isoquinolinyl, 6-Isoquinolinyl, 7-Isoquinolinyl, 8-Isoquinolinyl, 2-Quinoxolinyl, 5-Quinoxolinyl, 6-Quinoxolinyl, 1-Carbazoleyl, 2-Carbazoleyl, 3-Carbazoleyl, 4-Carbazoleyl, 9-Carbazoleyl, Azacarbazoleyl-1 -yl, azacarbazole-2-yl, azacarbazole-3-yl, azacarbazole-4-yl, azacarbazole-5-yl, azacarbazole-6-yl, azacarbazole-7-yl, azacarbazole-8-yl, azacarbazole-9-yl, 1-phenanthridyl, 2-phenanthridyl, 3-phenanthridyl, 4-phenanthridyl, 6-phenanthridyl, 7-phenanthridyl, 8-phenanthridyl, 9-phenanthridyl, 1 0-Phenyridyl, 1-Acridinel, 2-Acridinel, 3-Acridinel, 4-Acridinel, 9-Acridinel, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazonyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrole-1-yl, 2-Methylpyrrole-3-yl, 2-Methylpyrrole-4-yl, 2-Methylpyrrole -5-yl, 3-methylpyrrolo-1-yl, 3-methylpyrrolo-2-yl, 3-methylpyrrolo-4-yl, 3-methylpyrrolo-5-yl, 2-tert-butylpyrrolo-4-yl, 3-(2-phenylpropyl)pyrrolo-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophene, 2-dibenzothiophene, 3-dibenzothiophene, 4-dibenzothiophene, 1-naphtho-[1,2-[b]-benzofuranyl, 2-naphtho-[1,2-b]-benzofuranyl, 3-naphtho-[1,2-b]-benzofuranyl, 4-naphtho-[1,2-b]-benzofuranyl, 5-naphtho-[1,2-b]-benzofuranyl, 6-naphtho-[1,2-b]-benzofuranyl, 7-naphtho-[1,2-b]-benzofuranyl 8-Naphtho-[1,2-b]-benzofuranyl, 9-Naphtho-[1,2-b]-benzofuranyl, 10-Naphtho-[1,2-b]-benzofuranyl, 1-Naphtho-[2,3-b]-benzofuranyl, 2-Naphtho-[2,3-b]-benzofuranyl, 3-Naphtho-[2,3-b]-benzofuranyl, 4-Naphtho-[2, [3-b]-benzofuranyl, 5-naphtho-[2,3-b]-benzofuranyl, 6-naphtho-[2,3-b]-benzofuranyl, 7-naphtho-[2,3-b]-benzofuranyl, 8-naphtho-[2,3-b]-benzofuranyl, 9-naphtho-[2,3-b]-benzofuranyl, 10-naphtho-[2,3-b]-benzofuran 1-Naphtho-[2,1-b]-benzofuranyl, 2-Naphtho-[2,1-b]-benzofuranyl, 3-Naphtho-[2,1-b]-benzofuranyl, 4-Naphtho-[2,1-b]-benzofuranyl, 5-Naphtho-[2,1-b]-benzofuranyl, 6-Naphtho-[2,1-b]-benzofuranyl, 7-Naphtho-[2, 1-b]-benzofuranyl, 8-naphtho-[2,1-b]-benzofuranyl, 9-naphtho-[2,1-b]-benzofuranyl, 10-naphtho-[2,1-b]-benzofuranyl, 1-naphtho-[1,2-b]-benzothiophenyl, 2-naphtho-[1,2-b]-benzothiophenyl, 3-naphtho-[1,2-b]-benzothiophene 4-Naphtho-[1,2-b]-benzothiophene, 5-Naphtho-[1,2-b]-benzothiophene, 6-Naphtho-[1,2-b]-benzothiophene, 7-Naphtho-[1,2-b]-benzothiophene, 8-Naphtho-[1,2-b]-benzothiophene, 9-Naphtho-[1,2-b]-benzothiophene, 10-Naphtho-[1 [2,3-b]-benzothiophene, 1-naphtho-[2,3-b]-benzothiophene, 2-naphtho-[2,3-b]-benzothiophene, 3-naphtho-[2,3-b]-benzothiophene, 4-naphtho-[2,3-b]-benzothiophene, 5-naphtho-[2,3-b]-benzothiophene, 1-naphtho-[2,1-b]-benzothiophene 2-Naphtho-[2,1-b]-benzothiophene, 3-Naphtho-[2,1-b]-benzothiophene, 4-Naphtho-[2,1-b]-benzothiophene, 5-Naphtho-[2,1-b]-benzothiophene, 6-Naphtho-[2,1-b]-benzothiophene, 7-Naphtho-[2,1-b]-benzothiophene, 8-Naphtho-[2,1-b]-benzothiophene1-b]-benzothiophene, 9-naphtho-[2,1-b]-benzothiophene, 10-naphtho-[2,1-b]-benzothiophene, 2-benzofurano[3,2-d]pyrimidinyl, 6-benzofurano[3,2-d]pyrimidinyl, 7-benzofurano[3,2-d]pyrimidinyl, 8-benzofurano[3,2-d]pyrimidinyl, 9-benzofurano[3,2-d]pyrimidinyl, 2-benzothio[3,2-d]pyrimidinyl, 6-benzothio[3,2-d]pyrimidinyl, 7-benzothio[3,2-d]pyrimidinyl, 8-benzothio[3,2-d]pyrimidinyl, 9-benzothio[3,2-d]pyrimidinyl, 2-benzofurano[3,2-d]pyrazinyl 6-Benzofurano[3,2-d]pyrazinyl, 7-Benzofurano[3,2-d]pyrazinyl, 8-Benzofurano[3,2-d]pyrazinyl, 9-Benzofurano[3,2-d]pyrazinyl, 2-Benzothio[3,2-d]pyrazinyl, 6-Benzothio[3,2-d]pyrazinyl, 7-Benzothio[3,2-d]pyrazinyl Phosphine, 8-benzothio[3,2-d]pyrazine, 9-benzothio[3,2-d]pyrazine, 1-siliconyl, 2-siliconyl, 3-siliconyl, 4-siliconyl, 1-germaniumyl, 2-germaniumyl, 3-germaniumyl, 4-germaniumyl, 1-dibenzoselenyl, 2-dibenzoselenyl, 3-dibenzoselenyl, 4-dibenzoselenyl, etc. In this disclosure, the term "fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring" refers to a ring formed by fusion of at least one aliphatic ring having 3 to 30 carbon atoms in its ring skeleton (preferably 3 to 25, more preferably 3 to 18) and at least one aromatic ring having 6 to 30 carbon atoms in its ring skeleton (preferably 6 to 25, more preferably 6 to 18). For example, the fused ring can be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. In this document, the carbon atoms in the fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring can be replaced by at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. In this disclosure, the term "halogen" includes F, Cl, Br, and I.

[0032] Furthermore, "ortho (o)," "meta (m)," and "para (p)" indicate the substitution positions of all substituents. The ortho position is a compound with substituents adjacent to each other, specifically at positions 1 and 2 on benzene. The meta position is the next substitution position after the immediate adjacent substitution position, meaning the compound has substituents at positions 1 and 3 on benzene. The para position is the next substitution position after the meta position, meaning the compound has substituents at positions 1 and 4 on benzene.

[0033] In this disclosure, the term "ring formed by connection with adjacent substituents" refers to a substituted or unsubstituted (3-membered to 30-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof, preferably a substituted or unsubstituted (3-membered to 26-membered) monocyclic or polycyclic aliphatic ring, aromatic ring, or combination thereof, formed by connecting or fused two or more adjacent substituents. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably at least one heteroatom selected from the group consisting of N, O, and S. According to one embodiment of this disclosure, the number of atoms in the ring backbone is 5 to 20; according to another embodiment of this disclosure, the number of atoms in the ring backbone is 5 to 15. The linked or fused rings can be, for example, substituted or unsubstituted dibenzothiophene rings, substituted or unsubstituted dibenzofuran rings, substituted or unsubstituted naphthyl rings, substituted or unsubstituted phenanthrene rings, substituted or unsubstituted fluorene rings, substituted or unsubstituted benzothiophene rings, substituted or unsubstituted benzofuran rings, substituted or unsubstituted indole rings, substituted or unsubstituted indene rings, substituted or unsubstituted benzene rings, or substituted or unsubstituted carbazole rings, etc.

[0034] Furthermore, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or functional group (i.e., a substituent). Preferably, in this disclosure, the substituents of substituted (C1-C30)alkyl, substituted (C2-C30)alkenyl, substituted (C6-C30)aryl, substituted (3- to 30-membered)heteroaryl, substituted (C3-C30)cycloalkyl, substituted (3- to 7-membered)heteroalkyl, substituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring, substituted tri(C1-C30)alkylsilyl, substituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted (C1-C30)alkyldi(C6-C30)arylsilyl, and substituted tri(C6-C30)arylsilyl are each... Independently representing at least one group selected from the group consisting of: deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)ynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3- to 7-membered)heterocyclic alkyl, (C6-C30)aryloxy, (C6-C30)arylthio, unsubstituted or (C6-C30)aryl-substituted (5- to 30-membered)heteroaryl, unsubstituted or (5- to 30-membered)heteroaryl, tri(C1-C30) ... -C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, amino, mono- or di-(C1-C30)alkylamino, mono- or di-(C2-C30)alkenylamino, (C1-C30)alkyl(C2-C30)alkenylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, mono- or di-(3- to 30-membered)heteroarylamino (C1-C30)alkyl(3- to 30-membered)heteroarylamino, (C2-C30)alkenyl(C6-C30)arylamino, (C2-C30)alkenyl(3- to 30-membered)heteroarylamino, (C6-C30)aryl(3- to 30-membered)heteroarylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboroncarbonyl, di(C1-C30)alkylboroncarbonyl, (C1-C30)alkyl(C6-C30)arylboroncarbonyl, (C6-C30)aryl(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.For example, the substituents can be methyl, phenyl, naphthyl, p-phenyl, meta-phenyl, meta-terphenyl, fluorenyl, phenanthryl, pyridyl, dibenzothiophene, or dibenzofuranyl, etc.

[0035] The organic electroluminescent compound according to one embodiment will be described below.

[0036] According to one embodiment, the organic electroluminescent compound is represented by the following formula 1.

[0037]

[0038] In Equation 1,

[0039] R1 to R4 each independently represent *-(L1) a -(Ar1) b Hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings;

[0040] R5 to R 12 Each can be represented independently as *-(L1) a -(Ar1) b Hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl; or may be attached to one or more adjacent substituents to form one or more rings;

[0041] The premise is R1 to R 12 At least one of the following represents *-(L1) a -(Ar1) b ;

[0042] L1 represents a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0043] Ar1 represents substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, or -N-(Ar2)(Ar3);

[0044] Ar2 and Ar3 each independently represent substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C3-C30) aliphatic rings and (C6-C30) aromatic rings fused rings, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; and

[0045] a represents an integer of 1 or 2, and b represents an integer from 1 to 4; and when a and b are 2 or greater, each L1 and each Ar1 can be the same or different;

[0046] The premise is that compounds having Formula 1 are excluded, where R5 to R... 10 and R 12 Represents hydrogen, and R 11 Including substituted amino groups.

[0047] In one embodiment, R1 to R4 can each independently be *-(L1) a -(Ar1) b The substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl, preferably *-(L1). a -(Ar1) b The substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-membered to 25-membered) heteroaryl, more preferably *-(L1). a -(Ar1) b The R1 to R4 groups can each be independently a substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, or *-(L1). a -(Ar1) b .

[0048] In one embodiment, R5 to R 12 Each can be independently *-(L1) a -(Ar1) bHydrogen, fused ring groups of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted (C6-C30) aryl groups, or substituted or unsubstituted (3- to 30-membered) heteroaryl groups; or may be attached to one or more adjacent substituents to form one or more rings, preferably *-(L1). a -(Ar1) b Hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5- to 25-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aliphatic or aromatic rings, or combinations thereof, more preferably *-(L1). a -(Ar1) b Hydrogen, substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5- to 18-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more substituted or unsubstituted (5- to 30-membered) monocyclic or polycyclic aromatic rings.

[0049] In Equation 1 above, R1 to R 12 At least one of the following represents *-(L1) a -(Ar1) b For example, at least one of R1 to R4, at least one of R5 to R8, or R9 to R 12 At least one of them can be *-(L1) a -(Ar1) b For example, among R1 to R4, excluding *-(L1) a -(Ar1) b The other R1 through R4 can each independently be a substituted or unsubstituted methyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl. For example, R5 through R 12 Except for *-(L1) a -(Ar1) b R5 to R (other than) 12 Each can independently be hydrogen, an unsubstituted or (C6-C30) aryl or deuterium-substituted phenyl, a substituted or unsubstituted metaphenyl, or a substituted or unsubstituted pyridyl; or related to R5 to R 12 One or more adjacent substituents, or with R9 to R 12 One or more adjacent substituents can connect with each other to form a benzene ring, a naphthalene ring, or a phenanthrene ring.

[0050] According to one embodiment, Formula 1 can be an organic electroluminescent compound, wherein Ar1 represents a substituted or unsubstituted (3- to 30-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3); and L1 represents a single bond, or a substituted or unsubstituted (C6-C30) aryl group.

[0051] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of Formulas 1-1 to 1-4 below.

[0052]

[0053]

[0054] In equations 1-1 to 1-4,

[0055] R1 to R 12 L1, Ar1, a, and b are defined as in Equation 1 above.

[0056] According to another embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of Formulas 1-5 to 1-13 below.

[0057]

[0058]

[0059] In equations 1-5 to 1-13,

[0060] R1 to R 12 As defined in Equation 1 above;

[0061] R 13 To R 18 Each can be represented independently as *-(L1) a -(Ar1) b Hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C3-C30) aliphatic ring and (C6-C30) aromatic ring fused ring, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylsilyl, or substituted or unsubstituted tri(C6-C30) arylsilyl; or may be attached to one or more adjacent substituents to form one or more rings;

[0062] The premise is R1 to R in equations 1-5 to 1-7. 14 At least one of them, R1 to R in Equations 1-8 to 1-10 16 At least one of them, and R1 to R in formulas 1-11 to 1-13 18 At least one of the following represents *-(L1) a -(Ar1) b ;and

[0063] L1, Ar1, a, and b are defined as in Equation 1 above.

[0064] In one embodiment, Ar1 may be a substituted or unsubstituted (C6-C30) aryl, a substituted or unsubstituted (5- to 30-membered) heteroaryl, or -N-(Ar2)(Ar3), preferably a substituted or unsubstituted (5- to 25-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3), more preferably a substituted or unsubstituted (5- to 25-membered) heteroaryl containing at least one N, or -N-(Ar2)(Ar3). Ar2 and Ar3 can each independently be a fused ring of a substituted or unsubstituted (C3-C30) aliphatic ring and a (C6-C30) aromatic ring, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, preferably a fused ring of a substituted or unsubstituted (C3-C20) aliphatic ring and a (C6-C25) aromatic ring, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group, more preferably a fused ring of a substituted or unsubstituted (C3-C10) aliphatic ring and a (C6-C18) aromatic ring, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5- to 18-membered) heteroaryl group. For example, Ar2 and Ar3 can each independently be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted para-biphenyl, substituted or unsubstituted meta-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted... The group consists of substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzofluorenyl, or substituted or unsubstituted dihydrophenanthreneyl.

[0065] In one embodiment, the substituted or unsubstituted (C6-C30) aryl group in Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted phenanthyl group. Preferably, it may be an unsubstituted or deuterated or (5- to 30-membered) heteroaryl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted meta-biphenyl group, a substituted or unsubstituted meta-terphenyl group, or a substituted or unsubstituted naphthyl group.

[0066] In one embodiment, the substituted or unsubstituted (3-membered to 30-membered) heteroaryl group in Ar1 can be a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazine, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, or a substituted or unsubstituted benzoquinoxalinyl. Linolyl, substituted or unsubstituted dibenzoquinolinyl, substituted or unsubstituted dibenzoquinazolinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indonopyridyl, substituted or unsubstituted indonopyrazinyl, substituted or unsubstituted benzofuranopyridyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzofuranopyrazinyl, substituted or unsubstituted benzothiophenopyridyl, etc. Substituted or unsubstituted benzothiophene-pyrimidinyl, substituted or unsubstituted benzothiophene-pyrazinyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted benzocarbazoleyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiopheneyl, preferably substituted or unsubstituted pyridinyl, unsubstituted or (C6-C30) aryl-substituted carbazoleyl, substituted or unsubstituted benzocarbazoleyl, unsubstituted or (C6-C30) aryl-substituted And / or (5 to 30) heteroaryl-substituted quinazolinyl, unsubstituted or (C6-C30) aryl and / or (5 to 30) heteroaryl-substituted quinoxalinyl, unsubstituted or (C6-C30) aryl-substituted benzoquinoxalinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or unsubstituted or (C6-C30) aryl and / or (5 to 30) heteroaryl-substituted triazineyl.

[0067] In one embodiment, L1 can be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-element) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-element) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5- to 18-element) heteroarylene. For example, L1 can be a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted phenanthylene, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted triazine, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted dibenzofuranyl, or The substituted or unsubstituted benzoquinoxalinyl group, preferably, is a substituted or unsubstituted phenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted meta-biphenylene, a substituted or unsubstituted o-biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted triazine, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted benzoquinoxalinyl.

[0068] In one embodiment, a can be an integer of 1 or 2, b can be an integer of 1 or 2, and when a and b are 2, each L1 and Ar1 can be the same or different.

[0069] According to one embodiment, the organic electroluminescent compound represented by Formula 1 above can be further described by the following compounds, but is not limited thereto.

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] The organic electroluminescent compound having Formula 1 according to this disclosure can be produced as represented by reaction schemes 1 to 3 below, but is not limited thereto. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0098] [Reaction Scheme 1]

[0099]

[0100] [Reaction Scheme 2]

[0101]

[0102] [Reaction Scheme 3]

[0103]

[0104] In reaction schemes 1 to 3 above, R1 to R 12 L1 and Ar1 are defined as in Equation 1 above, and R 13 To R 16 As shown in equation 1 above, such as R5 to R 12 Defined.

[0105] As described above, exemplary synthetic examples of compounds represented by Formula 1 according to this disclosure are presented, but they are based on Suzuki cross-coupling reactions, Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, H-montmorillonite-mediated etherification reactions, Miyaura borylation reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, dehydration cyclization reactions, SN1 substitution reactions, SN2 substitution reactions, and phosphine-mediated reductive cyclization reactions, etc. Those skilled in the art will understand that the above reactions will continue even if other substituents defined in Formula 1 are bonded besides those described in the specific synthetic examples.

[0106] According to another embodiment, the organic electroluminescent compound can be represented by the following formula 2.

[0107]

[0108] In Equation 2,

[0109] R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings;

[0110] R'5 and R'6 each independently represent hydrogen or deuterium;

[0111] L'1 to L'3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0112] Ar' indicates a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0113] BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; and

[0114] m represents an integer from 1 to 4, n represents an integer from 1 to 3, and when m and n are 2 or greater, each R'5 and each R'6 can be the same or different.

[0115] In one embodiment, R'1 to R'4 can each independently be hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl, preferably substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-C25) aryl, more preferably substituted or unsubstituted (C1-C4) alkyl. For example, all R'1 to R'4 can be methyl.

[0116] In one embodiment, all R'5 and R'6 can be hydrogen or all R'5 and R'6 can be deuterium.

[0117] In one embodiment, L'1 to L'3 can each independently be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5- to 30-membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C25) arylene, or a substituted or unsubstituted (5- to 25-membered) heteroarylene, more preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, or a substituted or unsubstituted (5- to 18-membered) heteroarylene. For example, L'1 to L'3 can each independently be a single bond, or a substituted or unsubstituted phenylene, or a substituted or unsubstituted carbazolyl.

[0118] In one embodiment, Ar' can be a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (5- to 30-membered) heteroaryl, preferably a substituted or unsubstituted (C6-C25) aryl or a substituted or unsubstituted (5- to 25-membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C18) aryl or a substituted or unsubstituted (5- to 18-membered) heteroaryl. For example, Ar' can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, an unsubstituted or deuterated para-biphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuranyl.

[0119] In one embodiment, BFL may be a substituted or unsubstituted benzo[a]fluorenyl, a substituted or unsubstituted benzo[b]fluorenyl, or a substituted or unsubstituted benzo[c]fluorenyl, wherein the substituent of the substituted benzo[a]fluorenyl, the substituted benzo[b]fluorenyl, or the substituted benzo[c]fluorenyl may be deuterium, (C1-C10)alkyl, or (C6-C18)aryl, such as deuterium, methyl, or phenyl.

[0120] According to one embodiment, the organic electroluminescent compound represented by Formula 2 above can be further illustrated by the following compounds, but is not limited thereto.

[0121]

[0122]

[0123]

[0124] The organic electroluminescent compound having Formula 2 according to this disclosure can be produced by referring to the reactions represented by reaction schemes 1 to 3 above, but is not limited thereto. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0125] The organic electroluminescent compound according to other embodiments can be represented by the following formula 3.

[0126]

[0127] In Equation 3,

[0128] R' 11 To R' 14 Each can independently represent a substituted or unsubstituted methyl group;

[0129] R' 15 and R' 16 Each can be used independently to represent hydrogen or deuterium;

[0130] Ar' 11 and Ar' 12 Each of the following independently represents an unsubstituted or deuterated phenyl group, an unsubstituted or deuterated biphenyl group, an unsubstituted or deuterated terphenyl group, an unsubstituted or deuterated naphthyl group, an unsubstituted or deuterated group having the following formula (a), or a combination thereof:

[0131]

[0132] x represents an integer from 1 to 4, y represents an integer from 1 to 3, and when x and y are 2 or greater, each R' 15 and each R' 16 They can be the same or different.

[0133] In one embodiment, all R' 11 To R' 14 It can be an unsubstituted methyl group.

[0134] In one embodiment, all R'15 and R'16 may be hydrogen or all R'15 and R'16 may be deuterium.

[0135] In one embodiment, Ar' 11 and Ar' 12 Each of these can independently be an unsubstituted or deuterated phenyl group, an unsubstituted or deuterated biphenyl group, an unsubstituted or deuterated terphenyl group, an unsubstituted or deuterated naphthyl group, an unsubstituted or deuterated group having the above formula (a), or a combination thereof, preferably an unsubstituted phenyl group, an unsubstituted ortho-biphenyl group, an unsubstituted meta-biphenyl group, an unsubstituted or deuterated para-biphenyl group, an unsubstituted ortho-terphenyl group, an unsubstituted meta-terphenyl group, an unsubstituted para-biphenyl group, or an unsubstituted group having the above formula (a), or a combination thereof.

[0136] According to one embodiment, the organic electroluminescent compound represented by Formula 3 above can be further illustrated by the following compounds, but is not limited thereto.

[0137]

[0138]

[0139]

[0140] The organic electroluminescent compound having Formula 3 according to this disclosure can be produced by referring to the reactions represented by reaction schemes 1 to 3 above, but is not limited thereto. Furthermore, it can be prepared by synthetic methods known to those skilled in the art.

[0141] This disclosure may provide an organic electroluminescent material comprising an organic electroluminescent compound having Formula 1, and an organic electroluminescent device comprising said organic electroluminescent material.

[0142] Furthermore, this disclosure may provide an organic electroluminescent compound having Formula 2 and an organic electroluminescent device comprising said organic electroluminescent compound.

[0143] Furthermore, this disclosure may provide an organic electroluminescent compound having Formula 3 and an organic electroluminescent device comprising said organic electroluminescent compound.

[0144] According to one embodiment of this disclosure, the organic electroluminescent material may consist solely of an organic electroluminescent compound having Formula 1, or may further include conventional materials included in the organic electroluminescent material. In one embodiment, a compound having Formula 1 may be included as a hole transport material in a hole transport region. The hole transport region may be composed of one or more layers, said layers being the group consisting of a hole transport layer, a hole injection layer, an electron blocking layer, and a hole auxiliary layer, and each of said layers may be composed of one or more layers. In another embodiment, a compound having Formula 1 may be included as an electron transport material in an electron transport region. The electron transport region may be composed of one or more layers, said layers being the group consisting of an electron transport layer, an electron injection layer, a hole blocking layer, and an electron auxiliary layer, and each of said layers may be composed of one or more layers. In another embodiment, a compound having Formula 1 may be included as a host material in a light-emitting layer.

[0145] According to another embodiment of this disclosure, the organic electroluminescent compound represented by Formula 2 and / or the organic electroluminescent compound represented by Formula 3 can be included as a hole transport material in the hole transport region.

[0146] In addition to the organic electroluminescent compound having the above formula 1, the organic electroluminescent material disclosed herein may further include at least one host compound and at least one dopant.

[0147] The host material included in the organic electroluminescent material of this disclosure may further include an organic electroluminescent compound different from the organic electroluminescent compound having Formula 1 (the first host material) as a second host material. That is, the organic electroluminescent material according to one embodiment of this disclosure may include multiple host materials. Specifically, the multiple host materials according to one embodiment may include at least one compound having Formula 1 as a first host material, and at least one second host material different from the first host material. The weight ratio between the first host material and the second host material is from 1:99 to 99:1, preferably from 10:90 to 90:10, and more preferably from 30:70 to 70:30.

[0148] According to one embodiment, the second body material comprises a compound represented by Formula 11.

[0149]

[0150] In Equation 11,

[0151] L a It indicates a single bond, substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

[0152] Ara It indicates substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl;

[0153] R9 and R 10 Each of these elements independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 50-membered) heteroaryl, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic rings and (C6-C30) aromatic rings, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, or substituted or unsubstituted mono- or di-(C2-C30)alkenylamino. The following are substituted or unsubstituted (C1-C30) alkyl (C2-C30) alkenylamino, substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino, substituted or unsubstituted (C1-C30) alkyl (3- to 30-membered) heteroarylamino, substituted or unsubstituted (C2-C30) alkenyl (C6-C30) arylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, substituted or unsubstituted mono- or di- (3- to 30-membered) heteroarylamino, or substituted or unsubstituted (C6-C30) aryl (3- to 30-membered) heteroarylamino; or one or more adjacent substituents may be linked together to form one or more rings; and

[0154] f and g each independently represent integers from 1 to 4; and when f and g are 2 or greater, each R9 and each R 10 They can be the same or different.

[0155] According to one embodiment, the second body material represented by formula 11 can be represented by formula 12 or 13.

[0156]

[0157] In equations 12 and 13,

[0158] L a Ar a R9, R 10 And f is as defined in Equation 11 above;

[0159] T1 and T2 each independently represent a single bond, O, or S;

[0160] L b As in equation 11 above, such as L a Defined;

[0161] Ar b As in equation 11 above, such as Ar a Defined;

[0162] R 11 To R 14 Each is independently defined as R9 in Equation 11 above;

[0163] X1 represents O, S, or NR. a ;

[0164] R a Indicates substituted or unsubstituted (C6-C30) aryl; and

[0165] g' and h each independently represent integers from 1 to 3, i and k each independently represent integers from 1 to 4, and j represents an integer of 1 or 2; and when g', h, i, j, and k are 2 or greater, each R 10 Each R 11 Each R 12 Each R 13 and each R 14 They can be the same or different.

[0166] In one embodiment, L a and L b Each can be a single-bonded or substituted or unsubstituted (C6-C30) arylene, preferably a single-bonded or substituted or unsubstituted (C6-C25) arylene, and more preferably a single-bonded or substituted or unsubstituted (C6-C18) arylene. For example, L a and L b Each can be a single bond, a phenylene group, or a biphenylene group, independently.

[0167] In one embodiment, Ar a and Ar b Each can be independently a substituted or unsubstituted (C6-C30) aryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, more preferably an unsubstituted (C6-C25) aryl group or a (C6-C30) substituted (5- to 30-membered) heteroaryl group. For example, Ar a and Ar bEach of the following can be an unsubstituted or substituted phenyl group: methyl; cyano; triphenylsilane; phenyl; biphenyl; naphthyl; and unsubstituted or phenyl-substituted carbazolyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted meta-biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted fluorenyl, unsubstituted or phenyl-substituted naphthyl, or substituted or unsubstituted triphenylene.

[0168] In one embodiment, R a It can be a substituted or unsubstituted (C6-C30) aryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, more preferably an unsubstituted (C6-C25) aryl group or a (C6-C30) substituted (5- to 30-membered) heteroaryl group. For example, R a It may be an unsubstituted or substituted phenyl group, or a phenyl group substituted with at least one of the following: phenyl; biphenyl; naphthyl; and an unsubstituted or phenyl-substituted carbazolyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted meta-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, an unsubstituted or phenyl-substituted naphthyl, or a substituted or unsubstituted triphenylene.

[0169] In one embodiment, R9 to R 14 Each of these components can independently be hydrogen, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group, preferably hydrogen, a substituted or unsubstituted (C1-C10) alkyl group, a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5- to 25-membered) heteroaryl group, more preferably hydrogen, a substituted or unsubstituted (C1-C4) alkyl group, a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5- to 18-membered) heteroaryl group. For example, R9 to R 14 Each can be independently hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl.

[0170] According to one embodiment, the compound represented by Formula 11 can be more specifically exemplified by the following compounds, but is not limited thereto.

[0171]

[0172]

[0173]

[0174]

[0175] The compounds having Formula 11 according to this disclosure can be prepared by synthetic methods known to those skilled in the art.

[0176] The dopant included in the organic electroluminescent material of this disclosure can be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. There are no particular limitations on the phosphorescent dopant material used in this disclosure, but it can preferably be one or more metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) (if needed); more preferably, one or more ortho-metallized complexes of one or more metal atoms selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt) (if needed); and even more preferably, one or more ortho-metallized iridium complexes (if needed).

[0177] The dopants included in the organic electroluminescent devices of this disclosure may be compounds represented by formula 101, but are not limited thereto:

[0178]

[0179] In Equation 101,

[0180] L is selected from the following structures 1 to 3:

[0181]

[0182]

[0183] In structures 1 to 3

[0184] R 100 To R 103 Each of the following can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3- to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or one or more adjacent substituents may be connected to each other to form one or more rings, for example, to form one or more rings with pyridine, such as substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indoquinoline;

[0185] R 104 To R 107Each of these can independently represent hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or one or more adjacent substituents may be connected to each other to form one or more rings, for example, to form one or more rings with benzene, such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indopyridine, substituted or unsubstituted benzofuran-pyridine, or substituted or unsubstituted benzothiophene-pyridine;

[0186] R 201 To R 220 Each of these elements independently represents hydrogen, deuterium, halogen, unsubstituted or deuterated and / or halogenated (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or one or more adjacent substituents may be linked together to form one or more rings; and

[0187] s represents an integer from 1 to 3.

[0188] Specifically, examples of dopant compounds include, but are not limited to, the following.

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] In the following text, an organic electroluminescent device that applies the above-described organic electroluminescent compound and / or the above-described organic electroluminescent material will be described.

[0195] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer inserted between the first electrode and the second electrode. The organic layer may comprise at least one layer selected from the group consisting of: a hole transport layer, a hole injection layer, an electron blocking layer, a hole assist layer, a light-emitting assist layer, a light-emitting layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron assist layer, and each layer may further consist of several layers. Furthermore, the organic layer may further comprise at least one compound selected from the group consisting of: arylamine-based compounds and styrylarylamine-based compounds, and further comprise at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanides, and organometallic compounds of d-transition elements, or at least one complex compound comprising such metal.

[0196] The compounds represented by Formula 1 and / or Formula 2 in this disclosure may be included in one or more layers constituting an organic electroluminescent device. According to one embodiment, the organic layer includes a hole transport region and / or an electron transport region and / or a light-emitting layer containing an organic electroluminescent compound according to the invention, for example, a hole transport layer and / or a hole assist layer and / or a hole blocking layer and / or an electron assist layer and / or a light-emitting layer. For example, when a compound having Formula 1 is included in a hole transport layer and / or a hole assist layer and / or a hole blocking layer and / or an electron assist layer and / or a light-emitting layer, the compound having Formula 1 may be included as a hole transport material and / or a hole assist material and / or a hole blocking material and / or an electron assist material and / or a host material, respectively. The hole transport layer and / or the hole assist layer and / or the hole blocking layer and / or the electron assist layer and / or the light-emitting layer may include, for example, a single organic electroluminescent compound of this disclosure or a mixture of at least two organic electroluminescent compounds, and may further include conventional materials contained in the organic electroluminescent material.

[0197] According to one embodiment, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 1, for example, the hole transport layer may comprise at least one compound selected from compounds C-1 to C-700 represented by Formula 1. According to another embodiment, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 2, for example, the hole transport layer may comprise at least one compound selected from compounds C1-1 to C1-69 represented by Formula 2. According to other embodiments, the hole transport layer may comprise at least one organic electroluminescent compound represented by Formula 3, for example, the hole transport layer may comprise at least one compound selected from compounds C2-1 to C2-38 represented by Formula 3.

[0198] According to one embodiment, the light-emitting layer may comprise a plurality of host materials, said plurality of host materials including at least one first host material represented by Formula 1 and at least one second host material represented by Formula 11. According to one embodiment, the light-emitting layer may comprise at least one of compounds C-1 to C-700 represented by Formula 1 as a first host material and at least one of compounds H-1 to H-85 represented by Formula 11 as a second host material. According to another embodiment, the light-emitting layer may comprise an organic electroluminescent compound represented by Formula 2. For example, the light-emitting layer may comprise at least one compound of compounds C1-1 to C1-69 represented by Formula 2.

[0199] According to another embodiment, the hole blocking layer may contain at least one organic electroluminescent compound represented by Formula 1. For example, the hole blocking layer may contain at least one compound C-1 to C-700 represented by Formula 1.

[0200] According to one embodiment, the organic electroluminescent material can be used as a material for the organic layer in a white organic light-emitting device. Various structures have been proposed for white organic light-emitting devices based on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units, such as parallel side-by-side arrangements, stacked arrangements, or color conversion material (CCM) methods. Furthermore, according to one embodiment, the organic electroluminescent material can also be applied to organic electroluminescent devices containing QDs (quantum dots).

[0201] One of the first electrode and the second electrode can be an anode, and the other can be a cathode. The first electrode and the second electrode can each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials forming the first electrode and the second electrode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a side-emitting type.

[0202] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the emissive layer. The hole injection layer can be multilayered to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, wherein each of the multilayers can use two compounds simultaneously. The hole injection layer can be doped with a p-type dopant. Furthermore, an electron blocking layer can be placed between the hole transport layer (or hole injection layer) and the emissive layer, and can confine excitons within the emissive layer by blocking electrons from escaping from the emissive layer to prevent light leakage. The hole transport layer or electron blocking layer can be multilayered, and each layer can use multiple compounds.

[0203] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer can be multilayered to control electron injection and improve the interface properties between the light-emitting layer and the electron injection layer, wherein each of the multilayers can use two compounds simultaneously. The hole blocking layer or electron transport layer can also be multilayered, wherein each of the multilayers can use multiple compounds. Furthermore, the electron injection layer can be doped with an n-type dopant.

[0204] An auxiliary light-emitting layer can be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When placed between the anode and the light-emitting layer, it can promote hole injection and / or hole transport, or prevent electron overflow. When placed between the cathode and the light-emitting layer, it can promote electron injection and / or electron transport, or prevent hole overflow. Furthermore, a hole auxiliary layer can be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can effectively promote or limit the hole transport rate (or hole injection rate), thereby enabling charge balance control. When an organic electroluminescent device includes two or more hole transport layers, the further included hole transport layers can serve as hole auxiliary layers or electron blocking layers. The auxiliary light-emitting layer, hole auxiliary layer, or electron blocking layer can improve the efficiency and / or lifetime of the organic electroluminescent device.

[0205] In the organic electroluminescent device disclosed herein, it is preferable to place at least one layer (hereinafter referred to as "surface layer") selected from chalcogenide layers, metal halide layers, and metal oxide layers on one or more inner surfaces of one or two electrodes. Specifically, it is preferable to place silicon and aluminum chalcogenide (including oxide) layers on the anode surface of the electroluminescent dielectric layer, and it is preferable to place the metal halide layer or metal oxide layer on the cathode surface of the electroluminescent dielectric layer. The operational stability of the organic electroluminescent device can be obtained through the surface layer. Preferably, the chalcogenide includes SiO2. X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0206] Furthermore, in the organic electroluminescent device of this disclosure, it is preferable to place a mixed region of electron transport compound and reducing dopant, or a mixed region of hole transport compound and oxidizing dopant, on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, and thus it becomes easier to inject and transport electrons from the mixed region into the electroluminescent medium. Similarly, the hole transport compound is oxidized to cation, and thus it becomes easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopant includes various Lewis acids and acceptor compounds, and the reducing dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge-generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0207] To form each layer of the organic electroluminescent device of this disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating, etc., or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, flow coating, etc., can be used.

[0208] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer into any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material forming each layer can dissolve or diffuse and in which there are no problems with film-forming ability.

[0209] When a layer is formed using an organic electroluminescent compound according to one embodiment, the layer can be formed by the methods listed above, and typically by co-deposition or hybrid deposition. Co-deposition is a hybrid deposition method in which two or more materials are placed in respective individual crucible sources and current is simultaneously applied to two chambers to cause the materials to evaporate and to be co-deposited; and hybrid deposition is a hybrid deposition method in which two or more materials are mixed in a crucible source before being deposited and then current is applied to a chamber to cause the materials to evaporate.

[0210] According to one embodiment, the organic electroluminescent device disclosed herein can be used to manufacture display devices such as smartphones, tablets, laptops, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting.

[0211] In the following, the preparation methods of the compounds according to this disclosure will be explained with reference to representative compounds or intermediate compounds in order to provide a detailed understanding of this disclosure.

[0212] [Example 1] Synthesis of compound C1-14

[0213]

[0214] 1) Synthesis of Compound 1

[0215] 100.0 g (480 mmol) of phenanthrene-9,10-dione was added to a flask and dissolved in THF solution. Next, a solution of methyl magnesium bromide (MeMgBr) (3 M in THF) (480 mL, 1,440 mmol) was added dropwise at 0 °C under nitrogen purging, and the mixture was stirred for 2 hours. After the reaction was complete, the mixture was neutralized with aqueous ammonium chloride (NH4Cl) solution and extracted with chloromethane (MC), followed by drying with magnesium sulfate (MgSO4). The mixture was then separated by column chromatography, followed by the addition of methanol (MeOH). The resulting solid was then filtered under reduced pressure to obtain compound 1 (43.0 g, yield: 36%).

[0216] 2) Synthesis of Compound 2

[0217] Compound 1 (60.0 g, 250 mmol), H₂SO₄ (202 mL, 375 mmol), and 500 mL of benzene were added to a flask, and the mixture was stirred under reflux at 120 °C for 2 hours. After the reaction was complete, the mixture was neutralized with sodium bicarbonate (NaHCO₃), extracted with MC, and then dried over MgSO₄. Next, it was separated by column chromatography, followed by the addition of MeOH. The resulting solid was then filtered under reduced pressure to obtain compound 2 (50.0 g, yield: 90%).

[0218] 3) Synthesis of compound 3

[0219] Compound 2 (20.0 g, 90.0 mmol) was added to a flask and dissolved in THF solution. Next, a solution of MeMgBr (3 M in THF) (45 mL, 135 mmol) was added dropwise under nitrogen purging at 0 °C, and the mixture was stirred for 2 hours. After the reaction was complete, the mixture was neutralized with isopropanol (IPA) and aqueous NH4Cl solution, extracted with MC, and then dried over MgSO4. The mixture was then separated by column chromatography followed by the addition of MeOH. The resulting solid was then filtered under reduced pressure to obtain compound 3 (23.0 g, yield: 107%).

[0220] 4) Synthesis of compound 4

[0221] Compound 3 (18.6 g, 78 mmol) and 78 mL of thionyl chloride (1 M in MC) solution were added to a flask and stirred at 0 °C for 2 h. The temperature was lowered to -78 °C, and 78 mL of trimethylaluminum (AlMe3) (2 M in toluene) solution was added, followed by stirring for 3 h, and then reacted overnight at room temperature. After the reaction was complete, IPA and H2O were added to quench the solution, and the layers were separated by MC. Next, the layers were separated by column chromatography, followed by the addition of MeOH. The resulting solid was then filtered under reduced pressure to obtain compound 4 (18.7 g, yield: 101%).

[0222] 5) Synthesis of Compound 5

[0223] Compound 4 (19.2 g, 81 mmol) and 200 mL of DMF were added to a flask. N-bromosuccinimide (NBS) (26.0 g, 146 mmol) dissolved in 100 mL of DMF was added dropwise under nitrogen purging, followed by stirring. After the reaction was complete, ethyl acetate (EA) and H₂O were added, and the organic layer was then separated to remove the organic solvent. This was then separated by column chromatography, followed by the addition of MeOH. The resulting solid was then filtered under reduced pressure to obtain compound 5 (23.2 g, yield: 90%).

[0224] 6) Synthesis of compound C1-14

[0225] Compound 5 (5.59 g, 24.8 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluorene-2-amine (10.2 g, 24.8 mmol), tris(dibenzylacetone)dipalladium(0)(Pd2(dba)3) (0.81 g, 0.89 mmol), tri-tert-butylphosphine (P(t-Bu)3) (0.359 g, 1.77 mmol), sodium tert-butoxide (NaOt-Bu) (3.41 g, 35.5 mmol), and 60 mL of toluene were added to a flask and stirred at 120 °C for 1.5 h. After the reaction was complete, the organic solvent was removed, and the resulting solid was then separated by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compound C1-14 (1.3 g, yield: 11%).

[0226]

[0227]

[0228] [Example 2] Synthesis of compound C-14

[0229]

[0230] Compound 5 (6.0 g, 19.0 mmol), 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxapentoboran-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine (11.7 g, 22.8 mmol), Pd(PPh3)4 (1.10 g, 0.95 mmol), K2CO3 (7.9 g, 57 mmol), 50 mL of toluene, 25 mL of EtOH, and 25 mL of H2O were added to a flask and stirred under reflux at 140 °C. After the reaction was complete, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compound C-14 (2.4 g, yield: 20.3%).

[0231] MW color MP C-14 619.81 White 126℃

[0232] [Example 3] Synthesis of compound C-578

[0233]

[0234] 1) Synthesis of compound 1-1

[0235] 9,9,10,10-Tetramethyl-9,10-dihydrophenanthrene (34.0 g, 144 mmol), iodine (I₂) (18.3 g, 71.9 mmol), iodic acid (12.7 g, 71.9 mmol), 280 mL of acetic acid (AcOH), 36 mL of H₂SO₄, 36 mL of water (H₂O), and 15 mL of CHCl₃ were added to a flask and stirred at 65 °C. After the reaction was complete, the solvent was removed, and the mixture was then separated by column chromatography. Next, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 1-1 (56.0 g, yield: 107%).

[0236] 2) Synthesis of compounds 1-2

[0237] Compound 1-1 (35.0 g, 96.6 mmol), (5-chloro-2-formylphenyl)boronic acid (21.4 g, 116 mmol), Pd(PPh3)4 (5.58 g, 4.83 mmol), K2CO3 (33.4 g, 242 mmol), 300 mL of toluene, 100 mL of EtOH, and 100 mL of H2O were added to a flask and stirred at 140 °C. After the reaction was complete, EtOH and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, followed by separation by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compound 1-2 (36.0 g, yield: 99.4%).

[0238] 3) Synthesis of compounds 1-3

[0239] Compounds 1-2 (30.0 g, 80.0 mmol), chloro-(methoxymethyl)-triphenyl-λ5-phosphate (38.4 g, 112 mmol), and 370 mL of THF were added to a flask and dissolved. Subsequently, 112 mL of KOt-Bu (1 M in THF) solution was added dropwise with stirring. After the reaction was complete, EA and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, followed by separation by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compounds 1-3 (20.0 g, yield: 62.0%).

[0240] 4) Synthesis of compounds 1-4

[0241] Compounds 1-3 (19.0 g, 47.2 mmol) and 250 mL of MC were added to a flask and dissolved. Then, 17.8 mL of BF3·EtOEt solution was added dropwise at 0 °C with stirring. After the reaction was complete, MC and NaHCO3 (aqueous solution) were added to separate the layers, and then only the organic layer was separated. The solvent was removed by filtration under reduced pressure, followed by separation by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compounds 1-4 (16.0 g, yield: 91.5%).

[0242] 5) Synthesis of compound C-578

[0243] Compounds 1-4 (6.0 g, 16.2 mmol), N-phenyldibenzofuran-3-amine (4.40 g, 17.0 mmol), Pd2(dba)3 (0.741 g, 0.809 mmol), sphos (0.664 g, 1.62 mmol), NaOt-Bu (3.11 g, 32.4 mmol), and 80 mL of o-xylene were added to a flask and stirred under reflux at 180 °C. After the reaction was complete, the solvent was removed by filtration under reduced pressure, followed by separation by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compound C-578 (2.3 g, yield: 23.9%).

[0244] MW color MP C-578 593.27 White 188.4℃

[0245] [Example 4] Synthesis of compound C-470

[0246]

[0247] 1) Synthesis of compound 2-1

[0248] 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (30.0 g, 95.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (29.0 g, 114.1 mmol), PdCl2(PPh3)2 (3.34 g, 4.76 mmol), KOAc (23.3 g, 237.9 mmol), and 500 mL of 1,4-dioxane were added to a flask and stirred at 140 °C for 3 hours. After the reaction was complete, the organic solvent was removed, and the resulting solid was then separated by column chromatography. Next, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 2-1 (31 g, yield: 90%).

[0249] 2) Synthesis of compound C-470

[0250] Compound 2-1 (6.0 g, 16.6 mmol), 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (7.94 g, 18.2 mmol), Pd(PPh3)4 (0.960 g, 0.83 mmol), K2CO3 (6.88 g, 49.8 mmol), 40 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were added to a flask, and the mixture was stirred at 140 °C for 2 hours. After the reaction was complete, the organic solvent was removed, and the resulting solid was separated by column chromatography. Next, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound C-470 (4.5 g, yield: 44%).

[0251] MW color MP C-470 619.8 White 147.7℃

[0252] [Example 5] Synthesis of compound C-77

[0253]

[0254] Compound 2-1 (4.5 g, 12.4 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (4.65 g, 13.0 mmol), Pd(PPh3)4 (0.716 g, 0.62 mmol), K2CO3 (6.88 g, 31.0 mmol), 30 mL of toluene, 15 mL of EtOH, and 15 mL of H2O were added to a flask and stirred at 140 °C for 2 hours. After the reaction was complete, the organic solvent was removed, and the resulting solid was then separated by column chromatography. Next, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound C-77 (4.5 g, yield: 44%).

[0255] MW color MP C-77 557.68 White 198.1℃

[0256] [Example 6] Synthesis of compound C-652

[0257]

[0258] 1) Synthesis of compound 3-1

[0259] 10,10-Dimethylphenanthrene-9(10H)-one (10.0 g, 45.0 mmol) was added to a flask and then dissolved in THF solution. Next, a solution of phenylmagnesium bromide (PhMgBr) (3 M in THF) (22.5 mL, 67.5 mmol) was added dropwise at 0 °C under nitrogen purging and stirred for 2 hours. After the reaction was complete, the mixture was neutralized with aqueous NH4Cl solution and extracted with MC, followed by drying with MgSO4. The mixture was then separated by column chromatography. Subsequently, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound 3-1 (12.5 g, yield: 92%).

[0260] 2) Synthesis of compound C-652

[0261] Compound 3-1 (12.4 g, 41.3 mmol), N-([1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (65.6 g, 165 mmol), and 200 mL of MC were added to a flask and stirred at 0 °C. 6.7 mL of H₂SO₄ was added dropwise, and the reaction was allowed to proceed for one (1) day. After the reaction was complete, the mixture was neutralized with K₂CO₃ and extracted with MC, followed by drying with MgSO₄. It was then separated by column chromatography. MeOH was subsequently added, and the resulting solid was filtered under reduced pressure to obtain compound C-652 (8.6 g, yield: 31%).

[0262] MW color MP C-652 679.8 White 225.5℃

[0263] [Example 7] Synthesis of compound C-469

[0264]

[0265] 1) Synthesis of compound 4-1

[0266] 60.0 g (209 mmol) of 3-bromophenanthrene-9,10-dione was added to a flask and then dissolved in THF solution (1 L). Next, a solution of MeMgBr (3 M in THF) (209 mL, 627 mmol) was added dropwise at 0 °C under nitrogen purging, and the mixture was stirred for 1 hour. After the reaction was complete, MeMgBr was quenched with IPA and MeOH and H2O, and then neutralized with aqueous NH4Cl solution. The organic layer was then extracted with EA and dried over MgSO4. It was then separated through a diatomaceous earth filter, and MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compound 4-1 (74.0 g, yield: 110%).

[0267] 2) Synthesis of compounds 4-2 and 4-3

[0268] Compound 4-1 (74.0 g, 232 mmol), H₂SO₄ (18.9 mL, 348 mmol), and 1,000 mL of MC were added to a flask, and the mixture was stirred under reflux at 80 °C for 1 hour. After the reaction was complete, H₂O was added to the mixture to dilute the H₂SO₄, and the mixture was then neutralized with NaHCO₃. Next, it was extracted with MC and then dried over MgSO₄. Subsequently, it was separated by column chromatography, and then MeOH was added to it. The resulting solid was then filtered under reduced pressure to obtain compounds 4-2 and 4-3 (60.0 g, yield: 85%).

[0269] 3) Synthesis of compounds 4-4 and 4-5

[0270] Compounds 4-2 and 4-3 (60.0 g, 199 mmol) were added to a flask and then dissolved in THF solution (1 L). Subsequently, a MeMgBr (3 M in THF) solution (99.6 mL, 299 mmol) was added dropwise at 0 °C under nitrogen purging and stirring for 3 h. After the reaction was complete, the mixture was neutralized with aqueous IPA and NH4Cl, extracted with MC, and then dried over MgSO4. It was then separated by column chromatography, and MeOH was added. The resulting solid was then filtered under reduced pressure to obtain compounds 4-4 and 4-5 (63.2 g, yield: 100%).

[0271] 4) Synthesis of compounds 4-6

[0272] Compounds 4-4 and 4-5 (63.2 g, 199.2 mmol) and 183 mL of a solution of thionyl chloride (SOCl2) (1 M in MC) were added to a flask and stirred at 0 °C for 2 h. The temperature was lowered to -78 °C, and 183 mL of a solution of AlMe3 (2 M in toluene) was added, followed by stirring for 3 h, and then the reaction was allowed to proceed overnight at room temperature. After the reaction was complete, IPA and H2O were added to quench the solution, and the layers were separated by MC. Next, the layers were separated by column chromatography, and MeOH was added. The resulting solid was then filtered under reduced pressure to obtain compound 4-6 (59.0 g, yield: 94%).

[0273] 5) Synthesis of compound C-469

[0274] Compounds 4-6 (5.0 g, 15.7 mmol), N-([1,1'-biphenyl]-4-yl)-11,11-dimethyl-11H-benzo[b]fluorene-2-amine (8.45 g, 17.4 mmol), Pd2(dba)3 (0.719 g, 0.785 mmol), P(t-Bu)3 (0.318 g, 1.57 mmol), NaOt-Bu (3.02 g, 31.4 mmol), and 60 mL of toluene were added to a flask, and the mixture was stirred at 130 °C for 1 hour. After the reaction was complete, the organic solvent was removed, and the resulting solid was separated by column chromatography. Subsequently, MeOH was added, and the resulting solid was filtered under reduced pressure to obtain compound C-469 (2.1 g, yield: 19%).

[0275] MW color MP C-469 719.97 White 240℃

[0276] [Example 8] Synthesis of compound C-317

[0277]

[0278] Compound A (2.6 g, 6.64 mmol), di([1,1'-biphenyl]-4-yl)amine (2.1 g, 6.64 mmol), Pd2(dba)3 (0.3 g, 0.33 mmol), P(t-Bu)3 (0.3 mL, 0.66 mmol), NaOt-Bu (1.0 g, 9.96 mmol), and 33 mL of toluene were added to a reaction vessel and stirred under reflux for 1 hour. After the reaction was complete, the reaction mixture was cooled to room temperature and the solid was filtered and then washed with ethyl acetate. Next, the filtrate was distilled under reduced pressure and then purified by column chromatography to obtain compound C-317 (2.5 g, yield: 59%).

[0279] MW MP C-317 631.85 235℃

[0280] [Example 9] Synthesis of compound C-400

[0281]

[0282] Compound A (3.5 g, 8.94 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxapentoboran-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (4.7 g, 8.94 mmol), Pd(PPh3)4 (0.5 g, 0.45 mmol), Na2CO3 (2.4 g, 22.35 mmol), 45 mL of toluene, 11 mL of ethanol, and 11 mL of H2O were added to a reaction vessel, and the mixture was stirred at 120 °C for 4 hours. After the reaction was complete, the mixture was washed with distilled water and the organic layer was extracted with ethyl acetate. The extracted organic layer was then dried over magnesium sulfate. Next, the solvent was removed by rotary evaporator, and the mixture was purified by column chromatography to obtain compound C-400 (2.0 g, yield: 32%).

[0283] MW MP C-400 707.94 296℃

[0284] [Example 10] Synthesis of compound C2-31

[0285]

[0286] Compound 5 (6.5 g, 20.6 mmol), compound 10 (10.0 g, 20.6 mmol), Pd2(dba)3 (943 mg, 1.03 mmol), P(t-Bu)3 (1.0 mL, 2.06 mmol, 50% toluene solution), NaOt-Bu (3.0 g, 30.9 mmol), and 103 mL of toluene were added to a flask and refluxed for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was then removed by rotary evaporator. The mixture was purified by column chromatography to obtain compound C2-31 (5.3 g, yield: 36%) as a white solid.

[0287] MW MP C2-31 719.97 140℃

[0288] [Example 11] Synthesis of compound C2-8

[0289]

[0290] Compound 1-1 (9.0 g, 24.8 mmol), di([1,1'-biphenyl]-4-yl)amine (9.6 g, 29.8 mmol), Pd2(dba)3 (1.1 g, 1.24 mmol), P(t-Bu)3 (1.2 mL, 2.48 mmol, 50% toluene solution), NaOt-Bu (4.8 g, 49.6 mmol), and 130 mL of toluene were added to a flask and refluxed for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was then removed by rotary evaporator. The mixture was purified by column chromatography to obtain compound C2-8 (4.1 g, yield: 30%) as a white solid.

[0291] MW MP C2-8 555.77 154℃

[0292] [Example 12] Synthesis of compound C2-32

[0293]

[0294] 1) Synthesis of compound 12-1

[0295] Compound 1-1 (30.0 g, 82.8 mmol), 4-chloroaniline (21.7 g, 169.8 mmol), palladium(II) acetate (Pd(OAC)2) (1.3 g, 5.68 mmol), S-Phos (4.6 g, 11.3 mmol), NaOt-Bu (16.3 g, 169.8 mmol), and 566 mL of o-xylene were added to a flask and refluxed for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was then removed by rotary evaporator. The mixture was purified by column chromatography to obtain compound 12-1 (18 g, yield: 60%).

[0296] 2) Synthesis of compound 12-2

[0297] Compound 12-1 (18.0 g, 49.7 mmol), phenylboronic acid (13.2 g, 74.6 mmol), Pd(OAC)2 (559 mg, 2.49 mmol), S-Phos (2.0 g, 4.97 mmol), NaOt-Bu (12 g, 124.4 mmol), 250 mL of o-xylene, 60 mL of 1,4-dioxane, and 60 mL of distilled water were added to a flask and refluxed for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was then removed by rotary evaporator. The mixture was purified by column chromatography to obtain compound 12-2 (18.1 g, yield: 90%).

[0298] 3) Synthesis of compound C2-32

[0299] Compound 12-2 (10.2 g, 25.2 mmol), compound 12-3 (10.0 g, 25.2 mmol), Pd2(dba)3 (1.2 g, 1.26 mmol), P(t-Bu)3 (1.24 mL, 2.52 mmol, 50% toluene solution), NaOt-Bu (3.6 g, 37.8 mmol), and 126 mL of toluene were added to a flask, and the mixture was then refluxed for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the solvent was removed by rotary evaporator. The mixture was then purified by column chromatography to obtain compound C2-32 (5.9 g, yield: 33%) as a white solid.

[0300] MW MP C2-32 719.97 126℃

[0301] [Example 13] Synthesis of compound C-696

[0302]

[0303] 3-Bromo-9,9,10,10-tetramethyl-9,10-dihydrophenanthrene (5.5 g, 10.4 mmol), 2,4-diphenyl-6-(8-(4,4,5,5-tetramethyl-1,3,2-dioxapentylborane-2-yl)dibenzo[b,d]furan-1-yl)-1,3,5-triazine (4.3 g, 13.5 mmol), Pd(PPh3)4 (0.6 g, 0.52 mmol), K2CO3 (2.8 g, 20.8 mmol), 100 mL of toluene, 20 mL of H2O, and 20 mL of EtOH were added to a flask and stirred at 150 °C. After the reaction was complete, EA and H2O were added to the reaction mixture to separate the layers, and then only the organic layer was separated. Subsequently, the solvent was removed by filtration under reduced pressure, followed by separation by column chromatography. Next, MeOH was added, and the resulting solid was then filtered under reduced pressure to obtain compound C-696 (5.4 g, yield: 83%).

[0304] MW color MP C-696 633.8 White 129℃

[0305] [Example 14] Synthesis of compound C-697

[0306]

[0307] 1) Synthesis of Compound 11

[0308] 3-Bromo-9,9,10,10-Tetramethyl-9,10-dihydrophenanthrene (13.3 g, 42.1 mmol), (9H-carbazole-2-yl)boronic acid (13.3 g, 63.1 mmol), Pd(PPh3)4 (2.43 g, 2.1 mmol), K2CO3 (11.6 g, 84.2 mmol), 210 mL of toluene, 40 mL of H2O, and 20 mL of EtOH were added to a flask and stirred at 150 °C. After the reaction was complete, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by filtration under reduced pressure. Subsequently, it was separated by column chromatography, and then MeOH was added to it. Next, the resulting solid was filtered under reduced pressure to obtain compound 11 (6.9 g, yield: 40.8%).

[0309] 2) Synthesis of compound C-697

[0310] Compound 11 (6.9 g (15.9 mmol), 2-(4-bromophenyl)-4,6-dimethyl-1,3,5-triazine (6.8 g, 17.5 mmol), Pd(OAC)2 (0.18 g, 0.8 mmol), S-Phos (0.65 g, 1.59 mmol), NaOt-Bu (3.0 g, 31.8 mmol), and 160 mL of o-xylene were added to a flask, and the mixture was stirred at 180 °C. After the reaction was complete, only the organic layer was separated by adding EA and H2O, and the solvent was then removed by filtration under reduced pressure. Subsequently, it was separated by column chromatography, and MeOH was then added to it. Next, the resulting solid was filtered under reduced pressure to obtain compound C-697 (4.8 g, yield: 42.8%).

[0311] MW color MP C-697 708.9 White 300℃

[0312] [Example 15] Synthesis of compound C-572

[0313]

[0314] 1) Synthesis of compound 12

[0315] 9-Chloro-5,5,6,6-Tetramethyl-5,6-dihydrobenzo[k]butyronitrile (7.5 g, 20.2 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxapentylborane) (10.3 g, 40.4 mmol), Pd2(dba)3 (0.92 g, 1.01 mmol), S-Phos (0.83 g, 2.02 mmol), KOAC (4.95 g, 50.5 mmol), and 100 mL of 1,4-dioxane were added to a flask and then stirred at 180 °C. After the reaction was complete, only the organic layer was separated by adding MC and H2O, and then the solvent was removed by filtration under reduced pressure. Subsequently, it was separated by column chromatography, and then MeOH was added to it. Next, the resulting solid was filtered under reduced pressure to obtain compound 12 (9.6 g, yield: 95%).

[0316] 2) Synthesis of compound C-572

[0317] Compound 12 (9.6 g, 20.7 mmol), 2-chloro-4,6-dimethyl-1,3,5-triazine (5.3 g, 19.7 mmol), Pd(pph3)4 (1.13 g, 0.98 mmol), K2CO3 (5.4 g, 39.4 mmol), 200 mL of toluene, 40 mL of EtOH, and 40 mL of H2O were added to a flask and then stirred at 160 °C. After the reaction was complete, only the organic layer was separated by adding EA and H2O, and then the solvent was removed by filtration under reduced pressure. Subsequently, it was separated by column chromatography, and then MeOH was added to it. Next, the resulting solid was filtered under reduced pressure to obtain compound C-572 (8.5 g, yield: 80%).

[0318] MW color MP C-572 567.44 White 305℃

[0319] In the following sections, the luminescence characteristics of an organic electroluminescent device comprising an organic electroluminescent compound according to the present disclosure will be explained in order to provide a detailed understanding of the present disclosure.

[0320] [Apparatus Example 1-1] Fabrication of an OLED comprising an organic electroluminescent compound according to the present disclosure

[0321] OLEDs are produced using the organic electroluminescent compounds disclosed herein. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (GEOMATEC CO.,LTD., Japan) on a glass substrate for the OLED is subjected to ultrasonic washing sequentially with acetone, ethanol, and distilled water, and then stored in isopropanol before use. Vacuuming is performed until the vacuum level in the chamber reaches 10 Ω / sq.-6 After placement, the ITO substrate is mounted on the substrate support of a vacuum phase-deposition (VPD) apparatus. Then, compound HT-1 is introduced into one chamber of the VPD apparatus, and compound HI-1 is introduced into another chamber. Both materials are evaporated at different rates and deposited with a 3 wt% doping concentration to form a 10 nm thick hole injection layer on the ITO substrate. Next, compound HT-1 is introduced into one chamber of the VPD apparatus and evaporated by applying current to the chamber, thereby forming a first hole transport layer with a 90 nm thick on the hole injection layer. Next, compound C1-14, described in Table 1 below, is introduced into another chamber of the VPD apparatus and evaporated by applying current to the chamber, thereby forming a second hole transport layer with a 60 nm thick on the first hole transport layer. After forming the hole injection and hole transport layers, a light-emitting layer is formed thereon as follows: compound RH is introduced into one chamber of the VPD apparatus as the host, and compound D-39 is introduced into the other chamber as a dopant. Two materials were evaporated and a dopant was deposited at a dopant concentration of 2 wt% based on the total amount of the host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. Next, compounds ET and EI were evaporated at a 1:1 rate in two additional chambers to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer. Following this, after depositing compound EI as a 2 nm thick electron injection layer, an 80 nm thick Al cathode was deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0322] [Comparative Example 1-1] Preparation of OLEDs Containing Conventional Compounds

[0323] The OLED was produced in the same manner as in Device Example 1-1, except that the compound NPB was used as the material for the second hole transport layer.

[0324] The driving voltage, luminous efficiency, and color coordinates of the OLEDs manufactured as described above according to Device Example 1-1 and Comparative Example 1-1 were measured at a brightness of 1,000 nits, and the time taken for the brightness to decrease from 100% to 95% at a brightness of 10,000 nits (lifetime; T95) were also measured. The results are shown in Table 1-1 below:

[0325] Table 1-1

[0326]

[0327] [Device Examples 1-2 to 1-4] Fabrication of OLEDs comprising organic electroluminescent compounds according to the present disclosure

[0328] The OLED is produced in the same manner as in Device Example 1-1, except that compound RH-2 is used as the host of the light-emitting layer and the compounds described in Table 1-2 below are used as the materials for the second hole transport layer.

[0329] [Comparative Examples 1-2] Preparation of OLEDs Containing Conventional Compounds

[0330] The OLED is produced in the same manner as in Device Example 1-1, except that compound RH-2 is used as the host of the light-emitting layer and the compounds described in Table 1-2 below are used as the materials for the second hole transport layer.

[0331] The time (lifetime; T95) taken for the OLEDs manufactured as described above according to device examples 1-2 to 1-4 and comparative example 1-2 to decrease in brightness from 100% to 95% at a brightness of 10,000 nits was measured, and the results are shown in Table 1-2 below:

[0332] Table 1-2

[0333]

[0334]

[0335] By including the organic electroluminescent compound according to the present disclosure in the hole transport region, an organic electroluminescent device with low driving voltage, high luminous efficiency, and long lifespan can be provided.

[0336] [Device Examples 2-1 and 2-2] Fabrication of OLEDs comprising organic electroluminescent compounds according to the present disclosure

[0337] The production of an OLED according to this disclosure involves the following steps: First, a transparent electrode indium tin oxide (ITO) film (10 Ω / sq) (Geoma Co., Ltd., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Next, compound HI-1 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of the two materials to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80 nm. Then, compound HT-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole transport layer with a thickness of 30 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, the light-emitting layer is formed on top of them as follows: The compounds shown in Table 2 below are introduced as the host into one chamber of a vacuum vapor deposition apparatus, and compound D-50 is introduced as a dopant into another chamber. Simultaneously, the dopant material is evaporated at different rates and deposited with a doping amount of 10 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 40 nm on the hole transport layer. Next, compounds ET and EI are deposited as electron transport layer materials at a weight ratio of 40:60 to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI as an electron injection layer material with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED is produced. Each compound used for all materials is 10 -6 Purification is achieved through vacuum sublimation.

[0338] [Device Examples 2-3 and 2-4] Fabrication of OLEDs comprising various host materials according to the present disclosure

[0339] The OLED was produced in the same manner as in Device Example 2-1, except that the compounds shown in Table 2 below were used as host materials and the two host materials were evaporated at different rates of 1:2 to deposit the light-emitting layer.

[0340] [Comparative Example 2] Preparation of OLEDs Containing Conventional Compounds as the Main Body

[0341] Except that the compound CBP is used as the host material to deposit the light-emitting layer, and the compound BAlq is used as the material for the hole blocking layer to deposit a hole blocking layer with a thickness of 5 nm on the light-emitting layer, and then the compounds ET and EI are deposited as the materials for the electron transport layer in a weight ratio of 40:60 to form an electron transport layer with a thickness of 30 nm on the hole blocking layer, the OLED is produced in the same manner as in device example 2-1.

[0342] The driving voltage, luminous efficiency, power efficiency, and emission color of the OLEDs manufactured as described above according to Device Examples 2-1 to 2-4 and Comparative Example 2 were measured at a brightness of 1,000 nits, as well as the time taken for the brightness to decrease from 100% to 95% at a brightness of 20,000 nits (lifetime; T95), and the results are shown in Table 2 below:

[0343] Table 2

[0344]

[0345] By including the organic electroluminescent compound according to the present disclosure in the light-emitting layer and a variety of host materials containing the organic electroluminescent compound, a long-lifetime organic electroluminescent device can be provided that not only has a low driving voltage and excellent light-emitting characteristics, but also has a significantly improved lifetime compared to OLEDs containing conventional host materials.

[0346] [Apparatus Example 3-1] Preparation of an OLED comprising a compound according to the present disclosure

[0347] OLEDs are produced using the organic electroluminescent compounds disclosed herein. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geoma Co., Ltd., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone, ethanol, and isopropanol, and then stored in isopropanol before use. Vacuuming is performed until the vacuum level in the chamber reaches 10... -6After placement, the ITO substrate is mounted on the substrate support of a vacuum phase deposition (VPD) apparatus. Then, compound HT-1 is introduced into one chamber of the VPD apparatus, and compound HI-1 is introduced into another chamber. The two materials are evaporated at different rates, and each compound is deposited at a doping concentration of 3 wt% to form a hole injection layer with a thickness of 10 nm on the ITO substrate. Next, compound HT-1 is introduced into one chamber of the VPD apparatus and evaporated by applying current to the chamber, thereby forming a first hole transport layer with a thickness of 75 nm on the hole injection layer. Next, compound HT-3 is introduced into another chamber of the VPD apparatus and evaporated by applying current to the chamber, thereby forming a second hole transport layer with a thickness of 5 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: compound BH-1 is introduced into one chamber of the VPD apparatus as the host, and compound BD is introduced into the other chamber as a dopant. Subsequently, both materials were evaporated and a dopant was deposited at a dopant concentration of 2 wt% based on the total amount of the host and dopant to form a 20 nm thick light-emitting layer on the second hole transport layer. Next, compound C-14 was deposited as a hole-blocking material to form a 5 nm thick hole-blocking layer. Compounds ET and EI were evaporated at a 1:1 rate in two additional chambers to deposit a 30 nm thick electron transport layer on the hole-blocking layer. After depositing compound EI as a 2 nm thick electron injection layer, an 80 nm thick Al cathode was deposited using another vacuum vapor deposition apparatus. Thus, an OLED was produced.

[0348] [Comparative Example 3-1] Preparation of OLEDs Containing Conventional Compounds

[0349] The OLED was produced in the same manner as in device example 3-1, except that compounds ET and EI, which serve as electron transport layers, were evaporated at a 1:1 rate to deposit an electron transport layer with a thickness of 33 nm on the light-emitting layer without depositing a hole blocking layer.

[0350] The driving voltage, current efficiency, and CIE color coordinates of the OLEDs produced as described above according to Device Example 3-1 and Comparative Example 3-1 were measured at a brightness of 1000 nits, and the results are shown in Table 3-1 below:

[0351] Table 3-1

[0352]

[0353] [Apparatus Examples 3-2 and 3-3] Preparation of OLEDs comprising compounds according to the present disclosure

[0354] The OLED is produced in the same manner as in device example 3-1, except that compound BD-1 is used as a dopant material and the compounds shown in Table 3-2 below are used as materials for the hole blocking layer.

[0355] [Comparative Example 3-2] Preparation of OLEDs Containing Conventional Compounds

[0356] The OLED was produced in the same manner as in device example 3-1, except that compound BD-1 was used as a dopant material and compounds ET and EI were evaporated at a 1:1 rate to deposit an electron transport layer with a thickness of 35 nm on the light-emitting layer without depositing a hole blocking layer.

[0357] The driving voltage, current efficiency, and CIE color coordinates of the OLEDs manufactured as described above according to device examples 3-2 and 3-3 and comparative example 3-2 were measured at a brightness of 1000 nits, and the results are shown in Table 3-2 below:

[0358] Table 3-2

[0359]

[0360] By including the organic electroluminescent compound according to the present disclosure in the hole blocking layer, an organic electroluminescent device with low driving voltage and high luminous efficiency can be provided.

[0361] [Device Example 4] Fabrication of a Red-Light-Emitting OLED According to the Present Disclosure

[0362] The OLED according to this disclosure is manufactured as follows. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geoma Co., Ltd., Japan) on a glass substrate used in the OLED is subjected to ultrasonic washing sequentially with acetone and isopropanol, and then stored in isopropanol for use. The ITO substrate is then mounted on a substrate holder in a vacuum vapor deposition apparatus. Next, compound HI-1 is introduced into one chamber of the vacuum vapor deposition apparatus, and compound HT-1 is introduced into another chamber. The two materials are evaporated at different rates, and compound HI-1 is deposited with a doping amount of 3 wt% based on the total amount of the two materials to form a hole injection layer with a thickness of 10 nm. Next, compound HT-1 is deposited on the hole injection layer as a first hole transport layer with a thickness of 80 nm. Then, compound HT-4 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying a current to the chamber, thereby forming a second hole transport layer with a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and hole transport layer, the light-emitting layer is formed thereon as follows: The first and second host compounds shown in Table 4 are each introduced as hosts into two chambers of a vacuum vapor deposition apparatus, and compound D-39 is introduced as a dopant into the other chamber. The two host materials are evaporated at a 1:1 rate, while the dopant is evaporated at a different rate simultaneously. The dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and dopant to form a light-emitting layer with a thickness of 40 nm on the second hole transport layer. Next, compounds ET and EI are deposited as electron transport layer materials at a 50:50 weight ratio to form an electron transport layer with a thickness of 35 nm on the light-emitting layer. After depositing compound EI as an electron injection layer with a thickness of 2 nm on the electron transport layer, an Al cathode with a thickness of 80 nm is deposited on the electron injection layer using another vacuum vapor deposition apparatus. Thus, an OLED is produced. Each compound used for all materials is 10 -6 Purification is achieved through vacuum sublimation.

[0363] [Comparative Example 4] Preparation of OLEDs Containing Conventional Compounds as the Main Body

[0364] The OLED was produced in the same manner as in Device Example 4, except that only the compound CBP was used as the main body of the light-emitting layer.

[0365] The driving voltage, luminous efficiency, and emission color of the OLEDs manufactured as described above according to Device Example 4 and Comparative Example 4 were measured at a brightness of 1,000 nits, and the time (lifetime; T95) taken for the brightness to decrease from 100% to 95% at a brightness of 5,000 nits was also measured. The results are shown in Table 4 below:

[0366] Table 4

[0367]

[0368] The compounds used in the above apparatus examples and comparative examples are shown in Table 5 below:

[0369] Table 5

[0370]

[0371]

[0372] Furthermore, in the organic electroluminescent compounds represented by Formula 1 according to this disclosure, the LUMO (lowest unoccupied molecular orbital) energy level, HOMO (highest unoccupied molecular orbital) energy level, and triplet energy level of the compounds were measured, wherein R5 to R 12 Connecting to one or more adjacent substituents to form a benzene ring or a naphthalene ring, and the results are shown in Table 6 below:

[0373] Table 6

[0374]

[0375] *The structure was optimized using the Gaussian16 quantum chemistry computation program, hybrid density functional theory (hybrid DFT) (B3LYP) and the 6-31G(d) basis set, and the triplet state was calculated using TD-DFT (time-dependent DFT).

[0376] Referring to Table 6 above, in the organic electroluminescent compounds represented by Formula 1 according to this disclosure, even when R5 to R8 and / or R9 to R 12 When connected to one or more adjacent substituents to form a benzene ring or naphthalene ring, it can also be confirmed that it has an energy level that can be used as the core of the OLED material according to this disclosure.

Claims

1. An organic electroluminescent compound, represented by the following formula 2: in R'1 to R'4 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3- to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings; R'5 and R'6 each independently represent hydrogen or deuterium; L'1 to L'3 each independently represent a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar' indicates a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3- to 30-membered) heteroaryl group; BFL represents substituted or unsubstituted benzo[a]fluorenyl, substituted or unsubstituted benzo[b]fluorenyl, or substituted or unsubstituted benzo[c]fluorenyl; and m represents an integer from 1 to 4, n represents an integer from 1 to 3, and when m and n are 2 or greater, each R'5 and each R'6 can be the same or different.

2. The organic electroluminescent compound according to claim 1, wherein, The compound represented by Formula 2 is selected from the following compounds:

3. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.

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