Organic light-emitting diode and apparatus containing the same

Abstract

The present invention relates to an organic light emitting diode comprising an anode, a cathode, a first light emitting layer, a second light emitting layer, a first charge generating layer and a first electron transport stack, and a display or light emitting device comprising the same.

Description

Detailed description of the invention

[0001] [Technical Field] The present invention relates to an organic light-emitting diode and an apparatus including the same.

[0002] [Background of the Invention] Organic light-emitting diodes (OLEDs), which are self-emissive devices, offer a wide viewing angle, excellent contrast, rapid response, high brightness, superior drive voltage characteristics, and color reproduction. A typical OLED includes an anode, a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, EML, and ETL are thin films formed from organic compounds and / or organometallic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode electrode move to the EML via the HTL, and electrons injected from the cathode electrode move to the EML via the ETL. The holes and electrons recombine in the EML to generate excitons. When the exciton falls from the excited state to the ground state, light is emitted. The injection and flow of holes and electrons must be balanced, and as a result, OLEDs with the above structure have excellent efficiency.

[0004] Various organic electron diodes containing different electron transport materials are well known in this art. However, there is still a need to improve the performance of such devices, particularly the performance of multi-emissive layer OLEDs, especially in terms of efficiency and voltage.

[0005] Therefore, an object of the present invention is to provide an organic light-emitting diode that overcomes the shortcomings of the prior art, in particular a multi-light-emitting layer top-emission OLED having improved performance, including improved efficiency and improved voltage.

[0006] [Disclosure] This object includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge generation layer, and a first electron transport laminate, The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is disposed between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains a compound of formula (I), (Ar 1 -A c ) a [[ID=,16]]-X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is independently selected from C6-C 60 aryl or C2-C 42 heteroaryl, wherein Ar 1 each is independently selected from C6-C 12 aryl, C3-C 11 heteroaryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 )2, and may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, preferably O, and R 10 is C6-C 12 aryl, C3-C 12Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 1 Upper C6~C 12 Each aryl substituent, and Ar 1 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; A is C6~C 30 Selected independently of Aryl, Here, each of A is C6~C 12 Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; X is C2~C 42 Heteroaryl and C6-C 60Independently selected from the group consisting of aryls, Here, each of X is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Each aryl substituent, and C3-C3 on X 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; The molecular dipole moment of the compound of formula (I) is between 0D and 4D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 0, 1, or 2; Ar 2 C2~C 42 Heteroaryl and C6-C 60Independently selected from the group consisting of aryls, Here, Ar 2 Each is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 These are independent, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, or partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 2 Upper C6~C 12 Each aryl substituent, and Ar 2 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; Z is C6~C 30 Selected independently of Aryl, Here, each of Z is C6~C 12Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; G is selected such that the dipole moment of compound G-phenyl is between 1D and 7D; The first electron transport layer and the second electron transport layer do not contain electrodopant. This is achieved using organic light-emitting diodes.

[0007] The aforementioned objective is further achieved by an apparatus comprising the organic light-emitting diode of the present invention, which is a display device or an illumination device.

[0008] In a display device or light-emitting device, light may be emitted through a transparent cathode.

[0009] In a display device or light-emitting device, light may be emitted through a transparent anode.

[0010] [First electron transport layer] The first electron transport layer contains the compound of formula (I). (Ar 1 -A c ) a -X b (I).

[0011] The first electron transport layer may consist of a compound of formula (I). Alternatively, the first electron transport layer may consist of a mixture of the compound of formula (I) and one or more further compounds, none of which are electrodopants. The first electron transport layer may contain two or more compounds of formula (I). In particular, the first electron transport layer may consist of a mixture of the compound of formula (I) and further compounds known in the art as electron transport matrix compounds. Exemplary further electron transport matrix compounds that may be included are disclosed below.

[0012] In the compound of formula (I), group "A" (if present, i.e., when c>1) is the group Ar 1 and the spacer portion that connects X. The compound of formula (I) has two or more groups (Ar 1 -A c If it includes ), the base may or may not include spacer A independently.

[0013] In the compound of formula (I), a and b are independently 1 or 2. Alternatively, both a and b may be 1.

[0014] In the compound of formula (I), c is independently either 0 or 1.

[0015] Ar 1 C6~C 60 Aryl or C2~C 42 Heteroaryl, or C6~C 54 Aryl or C2~C 39 Heteroaryl, or C6~C 48 Aryl or C2~C 36 Heteroaryl, or C6~C 42 Aryl or C2~C36 heteroaryl, or C6-C 36 aryl or C2-C 30 heteroaryl, or C6-C 30 aryl or C2-C 24 is independently selected from heteroaryl.

[0016] Ar 1 is independently, C6-C 54 aryl, optionally C6-C 48 aryl, optionally C6-C 42 aryl, optionally C6-C 36 aryl, optionally C6-C 30 aryl, and optionally C6-C 24 aryl may be.

[0017] Ar 1 is independently, C2-C 42 heteroaryl, optionally C2-C 40 heteroaryl, optionally C2-C 36 heteroaryl, optionally C2-C 30 heteroaryl, and optionally C2-C 24 heteroaryl may be.

[0018] In one embodiment, Ar 1 is different from X.

[0019] Ar 1 may include two or more fused aromatic rings, preferably a system of three or more fused aromatic rings.

[0020] Ar 1 may contain at least one sp 3 -hybridized carbon atom.

[0021] Ar 1 is not incorporated into the aromatic ring structure and may contain at least one carbon-carbon sp 2 alkene bond.

[0022] Ar 1 is unsubstituted C2-C42 In embodiments independently selected from heteroaryls, the heteroatom is bonded by a single bond to Ar 1 It is bonded to the molecular structure.

[0023] Ar 1 This can be independently selected from the group consisting of phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, dibenzo-furanyl, di-dibenzofuranyl, pyrimidinyl, pyrazinyl, aryl-alkenyl, or a group having formula (IIa).

[0024] [ka]

[0025] During the ceremony, The asterisk symbol "*" indicates the bonding position where the base of equation (IIa) is attached to A; R 1 ~R 5 H, C6~C 12 Aryl and C3~C 10 They are independently selected from the group consisting of heteroaryls or C4-C5 heteroaryls.

[0026] Ar 1 This can be independently selected from the group consisting of phenyl, anthracenyl, fluorenyl, or the group of formula (IIa).

[0027] [ka]

[0028] In the formula, R 1 ~R 5 The component is selected independently from H and phenyl.

[0029] Ar 1 This may be the base of equation (IIa).

[0030] [ka]

[0031] R 1 ~R 5 At least two of them are not H.

[0032] Under equation (IIa), R is not H. 1 ~R 5 At least two of these may be in ortho positions relative to each other. R is not H. 1 ~R 5 At least one of these may be in the ortho position relative to the * position. In this regard, the two groups are in the ortho position relative to each other when they are bonded to adjacent carbon atoms of the benzene ring in formula (IIa).

[0033] Ar 1 It can be independently selected from one of the following groups.

[0034] [ka]

[0035] Here, the asterisk symbols "*" represent the bonding positions for bonding to A.

[0036] Ar 1 When substituted, each substituent can be independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl.

[0037] A is C6~C, either substituted or unsubstituted. 30 Aryl, or C6~C 24 Aryl, or C6~C 18 It can be selected independently of Aryl.

[0038] A can be independently selected from the group consisting of phenylene, naphthylene, biphenylene, and terphenylene, each of which may be substituted or unsubstituted.

[0039] A can be independently selected from one of the following groups or a combination thereof.

[0040] [ka]

[0041] Here, Ar 1 The bonding position for bonding to X can be freely selected and may preferably be as follows:

[0042] [ka]

[0043] When A is substituted, each substituent on A can be independently selected from the group consisting of phenyl and C1-C4 alkyl groups.

[0044] X is C2~C 39 Heteroaryl and C6-C 54 Aryl, arbitrarily C2~C 36 Heteroaryl and C6-C 48 Aryl, optionally C3~C 30 Heteroaryl and C6-C 42 Aryl, optionally C3~C 27 Heteroaryl and C6-C 36 Aryl, optionally C3~C 24 Heteroaryl and C6-C 30 Aryl, and optionally C3-C 21 Heteroaryl and C6-C 24 The groups can be independently selected from the aryl group, and each group may be substituted or not.

[0045] X is C2~C39 N-containing heteroaryl, C2~C 39 O-containing heteroaryl and C6-C 54 Aryl, arbitrarily C2~C 36 N-containing heteroaryl, C2~C 36 O-containing heteroaryl and C6-C 48 Aryl, optionally C3~C 30 N-containing heteroaryl, C3~C 30 O-containing heteroaryl and C6-C 42 Aryl, optionally C3~C 27 N-containing heteroaryl, C3~C 27 O-containing heteroaryl and C6-C 36 Aryl, optionally C3~C 24 N-containing heteroaryl, C3~C 24 O-containing heteroaryl and C6-C 30 Aryl, and optionally C3~C 21 N-containing heteroaryl, C3~C 21 O-containing heteroaryl and C6-C 24 It can be selected independently from the group consisting of aryls.

[0046] X is C2~C 39 N-containing heteroaryl and C6-C 54 Aryl, arbitrarily C2~C 36 N-containing heteroaryl and C6-C 48 Aryl, optionally C3~C 30 N-containing heteroaryl and C6-C 42 Aryl, optionally C3~C 27 N-containing heteroaryl and C6-C 36 Aryl, optionally C3~C 24 N-containing heteroaryl and C6-C 30 Aryl, and optionally C3~C 21 N-containing heteroaryl and C6-C 24 They can be independently selected from the group consisting of aryls. In this regard, each N-containing heteroaryl may be defined as containing one or more N atoms as the sole heteroatom.

[0047] X can be independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil, each of which may be substituted or unsubstituted.

[0048] X can be independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil, each of which may be substituted or unsubstituted.

[0049] X can be independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, and fluoranthenyl, and each of these may or may not be substituted.

[0050] X can be independently selected from one of the following groups.

[0051] [ka]

[0052] In the formula, the asterisk symbol "*" represents a bonding position where a group is attached to A.

[0053] When X is substituted, each substituent on X can be independently selected from the group consisting of phenyl, naphthyl, and biphenylyl.

[0054] If X is substituted, each substituted X group is:

[0055] [ka]

[0056] This is also acceptable. In the formula, the asterisk symbol "*" represents the bond position in which the group is attached to A.

[0057] The compound of formula (I) may be defined as not containing partial P=O. The compound of formula (I) may be defined as not containing P(=O)Aryl2. The compound of formula (I) may be defined as not containing P(=O)Alkyl2. The compound of formula (I) may be defined as not containing P(=O)Ph2. The compound of formula (I) may be defined as not containing P(=O)(CH3)2. The compound of formula (I) may be defined as not containing R'P(=O)R'' (wherein R' and R'' are bonded to each other to form a ring), that is, not containing a ring-phosphine oxide. The compound of formula (I) may be defined as not containing R'P(=O)R'' (wherein R' and R'' are bonded to each other to form a 7-membered ring).

[0058] The compound of formula (I) may be defined as not containing two P=O moieties. The compound of formula (I) may be defined as not containing two P(=O)Aryl2 molecules. The compound of formula (I) may be defined as not containing two P(=O)Alkyl2 molecules. The compound of formula (I) may be defined as not containing two P(=O)Ph2 molecules. The compound of formula (I) may be defined as not containing two P(=O)(CH3)2 molecules. The compound of formula (I) may be defined as not containing CN.

[0059] One or more of the following formulas may be excluded from the range of compounds of formula (I).

[0060] [ka]

[0061] The compounds of formula (I) may contain 6 to 14 aromatic or heteroaromatic rings, optionally 7 to 13 aromatic or heteroaromatic rings, optionally 7 to 12 aromatic or heteroaromatic rings, or optionally 9 to 11 aromatic or heteroaromatic rings. In this regard, each aromatic and heteroaromatic ring is a single aromatic ring, such as a 6-membered aromatic ring (e.g., phenyl), a 6-membered heteroaromatic ring (e.g., pyridyl), or a 5-membered heteroaromatic ring (e.g., pyrrolyl). In a system of fused (hetero)aromatic rings, each ring is considered a single ring in this respect. For example, naphthalene contains two aromatic rings.

[0062] The hybrid function of the compound of formula (I) is B3LYP and Gaussian 6-31G. * Using the ground system, the molecular dipole moment calculated by the TURBOMOLE V6.5 program package may be between 0D and 4D; or between 0D and 3.5D; or between 0D and 3.0D; or between 0D and 2.5D; or between 0D and 2.0D. In this regard, the dipole moment of a molecule containing an N atom

[0063]

number

[0064] This is given by the following formula:

[0065]

number

[0066] During the ceremony,

[0067]

number

[0068] are the partial charge and position of atom i in the molecule. The dipole moment is determined by semi-empirical molecular orbital methods. The geometry of the molecular structure is 6-31G * optimized using the hybrid function B3LYP with a basis system in the gas phase as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). When two or more conformations are possible, the conformation with the lowest total energy is selected to determine the bond length of the molecule.

[0069] In one embodiment, using the hybrid function B3LYP and Gaussian 6-31G * basis system, the LUMO energy level of the compound of formula (I) on an absolute scale with the vacuum energy level set to zero, calculated by the TURBOMOLE V6.5 program package, is -1.90 eV to -1.60 eV, preferably -1.87 eV to -1.65 eV, preferably -1.85 eV to -1.65 eV.

[0070] The compound of formula (I) can be selected from Compounds A-1 to A-29 in Table 1 below.

[0071] [Table 1] JPEG0007894816000014.jpg232169JPEG0007894816000015.jpg238169JPEG0007894816000016.jpg227169JPEG0007894816000017.jpg254169JPEG0007894816000018.jpg195169

[0072] In one embodiment, using the hybrid function B3LYP and Gaussian 6-31G *Using the ground system, the LUMO energy levels of the compound of equation (I) on an absolute scale with a vacuum energy level of zero, calculated by the TURBOMOLE V6.5 program package, are -1.90 eV to -1.60 eV, preferably -1.85 eV to -1.65 eV.

[0073] The first electron transport layer may be positioned between the light-emitting layer and the second electron transport layer. The first electron transport layer may be positioned in direct contact with the light-emitting layer. The first electron transport layer may be positioned so as to be "sandwiched and in contact" with the light-emitting layer and the second electron transport layer.

[0074] The first electron transport layer can have a thickness of less than 50 nm, optionally 1 to 30 nm, optionally 1 to 10 nm, or optionally 1 to 5 nm.

[0075] [Second electron transport layer] The second electron transport layer contains the compound of formula (II). (Ar 2 ) m -(Z k -G) n (II).

[0076] The second electron transport layer may consist of a compound of formula (II). Alternatively, the second electron transport layer may consist of a mixture of the compound of formula (II) and one or more further compounds, provided that none of the further compounds are electrodopants. The first electron transport layer may contain two or more compounds of formula (II). The second electron transport layer may consist of a mixture of the compound of formula (II) and further compounds known in the art as electron transport matrix compounds. Exemplary further electron transport matrix compounds that may be included are disclosed below.

[0077] In the compound of formula (II), the group "Z" (if present, i.e., when k>1) is the group Ar 2 And the spacer part that connects G. The compound of formula (II) has two or more groups (Z kIf -G) is included, the base may or may not include spacer Z independently.

[0078] In equation (II), m and n are independently 1 or 2. In equation (II), m and n may also be 1.

[0079] In equation (II), k is independently 0, 1, or 2. In equation (II), k may also independently be 1 or 2.

[0080] Ar 2 C2~C 39 Heteroaryl and C6-C 54 Aryl, arbitrarily C2~C 36 Heteroaryl and C6-C 48 Aryl, optionally C3~C 30 Heteroaryl and C6-C 42 Aryl, optionally C3~C 27 Heteroaryl and C6-C 36 Aryl, optionally C3~C 24 Heteroaryl and C6-C 30 Aryl, and optionally C3-C 21 Heteroaryl and C6-C 24 It can be selected independently from the group consisting of aryls.

[0081] Ar 2 C2~C 39 N-containing heteroaryl and C6-C 54 Aryl, arbitrarily C2~C 36 N-containing heteroaryl and C6-C 48 Aryl, optionally C3~C 30 N-containing heteroaryl and C6-C 42 Aryl, optionally C3~C 27 N-containing heteroaryl and C6-C 36 Aryl, optionally C3~C 24 N-containing heteroaryl and C6-C 30 Aryl, and optionally C3~C 21 N-containing heteroaryl and C6-C 24They can be independently selected from the group consisting of aryls. In this regard, each N-containing heteroaryl may be defined as containing one or more N atoms as the sole heteroatom.

[0082] Ar 2 It may include at least two fused five-membered or six-membered rings.

[0083] Ar 2 These can be independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil, and each of these may be substituted or unsubstituted.

[0084] Ar 2 This can be independently selected from the group consisting of dibenzoacridinyl, 1,3-diadinyl, 1,4-diadinyl, anthracenyl, triazinyl, phenatrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranil.

[0085] Ar 2 It can be independently selected from one of the following groups.

[0086] [ka]

[0087] Here, the asterisk symbol "*" represents the bonding position to be attached to Z.

[0088] Ar 2 When is replaced, Ar 2Each of the above substituents may be independently selected from the group consisting of phenyl, naphthyl, optionally β-naphthyl, pyridinyl, and biphenyl-yl, each of which may or may not be substituted.

[0089] Ar 2 When Ar 2 is substituted, each of the substituents on Ar

[0090] Z is independently C6 - C 24 aryl, or C6 - C 18 aryl, or C6 - C 12 aryl, and these may or may not be substituted.

[0091] Z may be selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene, each of which may or may not be substituted.

[0092] Z may be independently selected from one of the following groups.

[0093]

Chemical formula

[0094] Here, the bonding positions to Ar 2 and G can be freely selected.

[0095] When Z is substituted, each of the substituents on Z may be independently selected from the group consisting of phenyl and C1 - C4 alkyl.

[0096] G is the hybrid function B3LYP and Gaussian 6 - 31G *Using the base system, the compound G-phenyl is selected such that its dipole moment is between 1D and 7D, as calculated by the TURBOMOLE V6.5 program package. The unit of dipole moment, "Debye," is abbreviated as "D." The inventors have found that it is advantageous for the compound of formula (II) to contain a group having a specific polarity, i.e., a specific dipole moment within the above or below range. It has been further found that it is still advantageous for the compound of formula (II) to contain a further polar group (a second polar group) suitable for balancing the dipole moment of the first polar group so that the total dipole moment of the compound of formula (II) is lower (for example, if the compound is a symmetric molecule containing the same first and second polar groups, the dipole moment may be 0 Debye). Therefore, the compound of formula (II) cannot be characterized by referring to the total dipole moment of the compound. As a result, artificial compounds containing the polar group "G" and the nonpolar group "phenyl" are referred to instead. In this regard, the dipole moment of compounds containing an N atom

[0097]

number

[0098] This is given by the following formula:

[0099]

number

[0100] During the ceremony,

[0101]

number

[0102] is the partial charge and position of atom i in the molecule. The dipole moment is determined by the semi-empirical molecular orbital method. The geometry of the molecular structure is implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) and is 6-31G in the gas phase. * The optimization is performed using the hybrid function B3LYP, which has a base system. If two or more conformations are feasible, the conformation with the lowest total energy is selected to determine the bond length of the molecule. In this regard, the entire subgroup G encompasses all possible substituents that may be included.

[0103] G can be selected such that the dipole moment of compound G-phenyl is greater than 1D; optionally 2D or greater; optionally 2.5D or greater, optionally 2.5D or greater, optionally 3D or greater, and optionally 3.5D or greater. G can be selected such that the dipole moment of compound G-phenyl is less than or equal to 7D, optionally 6.5D or less, optionally 6D or less, optionally 5.5D or less, and optionally 5D or less. If two or more conformational isomers of compound G-phenyl are feasible, the average value of the dipole moments of the conformational isomers of G-phenyl is selected so that it is within this range. Conformational isomerism is a form of stereoisomerism, and isomers can interconvert simply by formally rotating around a single bond.

[0104] By selecting compound G-phenyl such that its dipole moment falls within the above range, electron injection from adjacent separate charge generation layers (CGLs) is improved, reducing the voltage of the OLED device and increasing the cd / A efficiency of the OLED device.

[0105] Examples of the compound "G-phenyl" are listed in Table 2 below, where the portion of each compound is shown.

[0106] [ka]

[0107] This identifies the "phenyl" portion in "G-phenyl".

[0108] [Table 2] JPEG0007894816000026.jpg240169JPEG0007894816000027.jpg233169JPEG0007894816 000028.jpg244169JPEG0007894816000029.jpg238169JPEG0007894816000030.jpg23916 9JPEG0007894816000031.jpg244169JPEG0007894816000032.jpg255169JPEG0007894816 000033.jpg228169JPEG0007894816000034.jpg253169JPEG0007894816000035.jpg98169

[0109] G includes dialkylphosphinyls, diarylphosphinyls, alkylarylphosphinyls, diheteroarylphosphinyls, arylheteroarylphosphinyls, cyclic diarylphosphinyls, phosphine oxides, aryl-containing phosphine oxides, heteroaryl-containing phosphine oxides, cyclic arylheteroarylphosphinyls, cyclic heteroaryl-containing phosphine oxides, nitriles, benzonitriles, nicotinonitriles, amides, carbamides, and C2-C 42 It may be selected from the group consisting of heteroaryls; G may include one or more substituents bonded to the base, where one or more substituents are C6-C6 18 Aryl, C1~C 10 Alkyl, C2~C 14 It is selected from the group consisting of heteroaryls. In this regard, "cyclic" means that the "P=O" of phosphinyl and the phosphine oxide, respectively, are part of a ring formed together with further parts of the group.

[0110] G is G-C1~C10 Alkylphosphenyl, di-C6~C 10 Arylphosfinyl, C 10 ~C 42 Diheteroarylphosfinyl, C7~C 42 Aryl heteroarylphosphinyl, C8~C 42 Phosphine oxide, C8~C 42 Aryl-containing phosphine oxide, C8~C 63 Heteroaryl-containing phosphine oxide, C 12 ~C 63 Cyclic arylphosphinyl, C7~C 42 Cyclic arylheteroarylphosphinyl, C7~C 42 Cyclic heteroaryl-containing phosphine oxide, and C2-C 39 Heteroaryl, optionally C2-C 35 Heteroaryl, optionally C2-C 32 Heteroaryl, optionally C2-C 29 Heteroaryl, optionally C2-C 25 It may be selected from the group consisting of heteroaryls; G may include one or more substituents bonded to the base, where one or more substituents are C6-C6 12 Aryl, C1-C6 alkyl, C2-C 11 Selected from the group consisting of heteroaryls.

[0111] G is di-C1~C4 alkylphosphenyl, di-C6~C 10 Arylphosfinyl, C 10 Diheteroarylphosfinyl, C7~C 25 Aryl heteroarylphosphinyl, C8~C 42 Phosphine oxide, C8~C 42 Aryl-containing phosphine oxide, C8~C 24 Heteroaryl-containing phosphine oxide, C 12 ~C 42 Cyclic arylphosphinyl, C7~C 25 Cyclic arylheteroarylphosphinyl, C7~C 25 Cyclic heteroaryl-containing phosphine oxide, and C2-C 25The group consisting of heteroaryls may be selected; each G may include one or more substituents attached to the base, where the one or more substituents are C6-C6 10 The group is selected from aryl, C1-C4 alkyl, and C2-C5 heteroaryl compounds.

[0112] G includes dialkylphosphinyls, diarylphosphinyls, alkylarylphosphinyls, diheteroarylphosphinyls, arylheteroarylphosphinyls, cyclic diarylphosphinyls, phosphine oxides, aryl-containing phosphine oxides, heteroaryl-containing phosphine oxides, cyclic arylheteroarylphosphinyls, cyclic heteroaryl-containing phosphine oxides, nitriles, benzonitriles, nicotinonitriles, amidoyl, carbamidoyl, and C2-C 17 Selected from the group consisting of heteroaryls; each G may contain one or more substituents bonded to the base, where one or more substituents are selected from the group consisting of phenyl, methyl, ethyl, and pyridyl.

[0113] G is dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, dihydro-benzimidazolone-yl, diphenylpropane-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, phenylbenzoquinolinyl, phenylbenzimidazolone, pyridinyl, bipyridinyl, picolinyl, lutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenylpyradinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl, quinazolinyl, benzoxazolyl, benzimidazolyl, pyridinyl-imidazopyridinyl;

[0114] [ka] JPEG0007894816000037.jpg213169JPEG0007894816000038.jpg163169JPEG0007894816000039.jpg207169

[0115] It can be independently selected from the group consisting of the following. In the formula, the asterisk symbol "*" represents a bonding position.

[0116] G is dimethylphosphinyl, diphenylphosphinyl, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridinyl, 2,2'-bipyridinyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinyl, 2-quinazolinyl, 4-quinazolinyl, 4-phenyl-2-quinazolinyl, and (pyridin-2-yl)imidazo[1,5-a]pyridinyl;

[0117] [ka] JPEG0007894816000041.jpg211169JPEG0007894816000042.jpg168169JPEG0007894816000043.jpg212169JPEG0007894816000044.jpg87169

[0118] It can be independently selected from the group consisting of the following. In the formula, the asterisk symbol "*" represents a bonding position.

[0119] The compound of formula (II) may be selected from compounds B-1 to B-25 in Table 3 below.

[0120] [Table 3] JPEG0007894816000046.jpg227169JPEG0007894816000047.jpg227169JPEG0007894816000048.jpg227169 JPEG0007894816000049.jpg232169JPEG0007894816000050.jpg211169JPEG0007894816000051.jpg103169

[0121] In one embodiment, the hybrid function B3LYP and Gaussian 6-31G * Using the ground system, the LUMO energy levels of the compound of equation (II) on an absolute scale with a vacuum energy level of zero, calculated by the TURBOMOLE V6.5 program package, are in the range of -2.30 eV to -1.20 eV, preferably -2.10 eV to -1.28 eV.

[0122] In one embodiment, the compound of formula (II) contains one polar group "G".

[0123] The compound of formula (II) may be defined as not containing partial P=O. The compound of formula (II) may be defined as not containing P(=O)Aryl2. The compound of formula (II) may be defined as not containing P(=O)Alkyl2. The compound of formula (II) may be defined as not containing P(=O)Ph2. The compound of formula (II) may be defined as not containing P(=O)(CH3)2. The compound of formula (II) may be defined as not containing R'P(=O)R'' (wherein R' and R'' are bonded to each other to form a ring), that is, not containing a ring-phosphine oxide. The compound of formula (II) may be defined as not containing R'P(=O)R'' (wherein R' and R'' are bonded to each other to form a 7-membered ring).

[0124] The compound of formula (II) may be defined as not containing two P=O moieties. The compound of formula (II) may be defined as not containing two P(=O)Aryl2 molecules. The compound of formula (II) may be defined as not containing two P(=O)Alkyl2 molecules. The compound of formula (II) may be defined as not containing two P(=O)Ph2 molecules. The compound of formula (II) may be defined as not containing two P(=O)(CH3)2 molecules. The compound of formula (II) may be defined as not containing CN.

[0125] One or more of the following formulas may be excluded from the range of compounds of formula (II).

[0126] [ka]

[0127] If the second electron transport layer contains the compound of formula (II) and compound (III), the following combinations of the specified amounts of the compounds (see Tables 3 and 4) may be specified as being excluded.

[0128] B-23:C-3 30:70 v:v; C-3:B-10 30:70 v:v; B-23:C-5 30:70 v:v; B-10:C-5 30:70 v:v; B-23:C-6 30:70 v:v; B-10:C-6 30:70 v:v.

[0129] The following compounds

[0130] [ka]

[0131] The following organic light-emitting diodes a) and b) may be excluded: a) The electron transport layer is compound E

[0132] [ka]

[0133] A tandem OLED is provided, adjacent to and in direct contact with an n-doped charge generation layer made of metallic lithium (with a weight ratio of E:Li equal to 98:2), the composition of which is selected from B-23:C-3, B-10:C-3, B-23:C-5, B-10:C-5, B-23:C-6, and B-10:C-6, with a weight ratio of 30:70 between the first and second components in each of these compositions; b) A top-emission blue OLED having the following structure

[0134] [Table 4]

[0135] (In the table, HT-3 is

[0136] [ka]

[0137] And F2 is

[0138] [ka]

[0139] And C-1 is

[0140] [ka]

[0141] And D-1 is

[0142] [ka]

[0143] (H09 is a commercially available blue light-emitting host, and BD200 is a commercially available blue emitter, both supplied by SFC of Korea).

[0144] The second electron transport layer may further contain compound (III), where compound (III) comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, where one or more aromatic or heteroaromatic rings may be substituted with C1-C4 alkyl groups. In this regard, each aromatic ring and heteroaromatic ring is a single aromatic ring, such as a 6-membered aromatic ring like phenyl, a 6-membered heteroaromatic ring like pyridyl, and a 5-membered heteroaromatic ring like pyrrolyl. In a system of condensed (hetero)aromatic rings, each ring is considered a single ring in this respect. For example, naphthalene contains two aromatic rings.

[0145] Compound (III) may contain at least one heteroaromatic ring, optionally one to five heteroaromatic rings, optionally one to four heteroaromatic rings, optionally one to three heteroaromatic rings, and optionally one or two heteroaromatic rings.

[0146] The aromatic ring or heteroaromatic ring of compound (III) may be a six-membered ring.

[0147] The heteroaromatic rings of compound (III) may be N-containing heteroaromatic rings, and optionally all heteroaromatic rings may be N-containing heteroaromatic rings, and optionally all heteroaromatic rings may contain N as the sole heteroatom.

[0148] Compound (III) may contain at least one six-membered heteroaromatic ring containing 1 to 3 N atoms in each heteroaromatic ring, and optionally 1 to 3 six-membered heteroaromatic rings each containing 1 to 3 N atoms.

[0149] The at least one six-membered heteroaromatic ring in compound (III) may be an azine. The at least one six-membered heteroaromatic ring in compound (III) may be a triazine, a diazine, or a pyrazine.

[0150] If compound (III) contains two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring that does not contain heteroatoms.

[0151] In one embodiment, the heteroatoms in the heteroaromatic ring of compound (III) are bonded to the molecular structure of compound (III) by at least one double bond.

[0152] The hybrid functions of compound (III), B3LYP and Gaussian 6-31G * Using the ground system, the molecular dipole moment calculated by the TURBOMOLE V6.5 program package may be between 0D and 4D; or between 0.1D and 3.9D; or between 0.2D and 3.7D; or between 0.3D and 3.5D.

[0153] By selecting compound (III) described in these embodiments, the mobility of the second electron transport layer is further improved, the voltage of the OLED device is reduced, and the cd / A efficiency of the OLED device is increased.

[0154] In one embodiment, compound (III) is not the compound of formula (II). The compound of formula (III) can be selected from compounds C-1 to C-6 in Table 4 below.

[0155] [Table 5] JPEG0007894816000061.jpg114169

[0156] If the second electron transport layer contains both compound (II) and compound (III), the weight ratio of compound (II) to compound (III) may be 1:99 to 99:1, or 10:90 to 60:40, or 20:80 to 50:50, or 25:75 to 40:60, or approximately 30:70.

[0157] In one embodiment, the hybrid function B3LYP and Gaussian 6-31G * Using the ground system, the LUMO energy levels of the compound of equation (III) on an absolute scale with a vacuum energy level of zero, calculated by the TURBOMOLE V6.5 program package, are in the range of -2.00 eV to -1.70 eV, preferably -1.95 eV to -1.80 eV.

[0158] In one embodiment, compound (III) contains one nitrogen-containing six-membered ring.

[0159] In another embodiment, compound (III) comprises two nitrogen-containing six-membered rings.

[0160] In one embodiment, the compound of formula (I) is not the compound of formula (II). In a further embodiment, the compound of formula (II) is not the compound of formula (III). In another embodiment, the compound of formula (I) is not the compound of formula (III). In a further embodiment of the present invention, all three compounds, namely the compound of formula (I), the compound of formula (II), and the compound of formula (III), are different from one another in that they have different molecular structural formulas.

[0161] The second electron transport layer may be positioned between the first electron transport layer and the electron injection layer. The second electron transport layer may be positioned in direct contact with the first electron transport layer.

[0162] The second electron transport layer may be positioned so as to be "sandwiched and in contact" between the first electron transport layer and the electron injection layer.

[0163] The second electron transport layer may be positioned between the first electron transport layer and the charge generation layer. The second electron transport layer may be positioned in direct contact with the charge generation layer. The second electron transport layer may be positioned in direct contact with the n-type CGL.

[0164] The second electron transport layer may be positioned so as to be "sandwiched and in contact" between the first electron transport layer and the n-type CGL.

[0165] The second electron transport layer can have a thickness of less than 100 nm, arbitrarily 10-90 nm, arbitrarily 10-60 nm, or arbitrarily 10-50 nm.

[0166] [Further potential characteristics of OLEDs] The organic light-emitting diode according to the present invention includes at least two light-emitting layers, namely a first light-emitting layer and a second light-emitting layer. The organic light-emitting diode may further include additional light-emitting layers (such as a third light-emitting layer and a fourth light-emitting layer). When the organic light-emitting diode includes three or more light-emitting layers, only one electron transport laminate may be provided between two of the light-emitting layers. Alternatively, two or more electron transport laminates may be present. For example, when the organic light-emitting diode includes a first light-emitting layer, a second light-emitting layer and a third light-emitting layer, a first electron transport laminate may be placed between the first light-emitting layer and the second light-emitting layer, and a second electron transport laminate may be placed between the second light-emitting layer and the third light-emitting layer.

[0167] If the organic light-emitting diode includes three or more light-emitting layers, there may be two or more charge-generating layers. For example, if the organic light-emitting diode includes a first light-emitting layer, a second light-emitting layer, and a third light-emitting layer, a first charge-generating layer may be placed between the first light-emitting layer and the second light-emitting layer, and a second charge-generating layer may be placed between the second light-emitting layer and the third light-emitting layer.

[0168] In relation to this disclosure, a laminate is an array of two or more distinct layers. The layers of the laminate may be distinguished from one another by the chemical properties of the materials contained in each layer, i.e., they may be made of different compounds. An electron transport laminate according to this disclosure comprises at least two distinct layers, each made of an electron transport material.

[0169] The compound of formula (I) and the compound of formula (II) may be different from each other. That is, the compound of formula (I) and the compound of formula (II) may be different from each other in respect to at least one structural aspect, and in particular, they may be different in respect to at least one atom and / or group.

[0170] The first electron transport layer and the second electron transport layer do not contain electrodopants. In this regard, "do not contain" means that each layer contains only the respective compounds (electrodopants) that cannot be avoided by ordinary purification methods and general technical means during the preparation of each layer. In this regard, the electrodopant is, in particular, an electron-dopant, but is not limited to these. The electron-dopant may be selected from metals, or alkali metals, metal salts, or alkaline earth metal salts and / or rare earth metal salts, or organoalkali metal complexes, or alkali metal complexes, or LiF, LiCl, LiBr, LiI, LiQ, borate metal salts, or mixtures thereof. In particular, the first electron transport layer and the second electron transport layer do not have to contain electron-dopants. The electron-dopant may be a metal salt containing at least one metal cation and at least one anion. The metal cation of the metal salt may be selected from the group consisting of alkali metals, alkaline earth metals, and rare earth metals, or from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, and Ba; or from Li, Mg, Ca, and Sr. The anion of the metal salt may be selected from the group consisting of quinolinolates, phosphine oxide phenolates, and borooxide salts.

[0171] In this regard, electric n-dopant is particularly an elemental metal, or an electrically positive metal selected from alkali metals, alkaline earth metals, rare earth metals, and transition metals; a metal salt, or an alkali metal salt, alkaline earth metal salt, and / or rare earth metal salt; or a metal complex, or an alkali metal complex, alkaline earth metal complex, transition metal complex, and / or rare earth metal complex. Examples of n-doping metal salts may be LiF, LiCl, LiBr, LiI, metal borates, metal quinolinolates, or mixtures thereof. A further example of electric n-dopant is a potent chemical reducing agent. This type of "reductive" n-dopant can generally be characterized by the energy level of its highest occupied molecular orbital (HOMO) being comparable to the lowest unoccupied molecular orbital energy level of the corresponding electron transport matrix, which is about -3.0 eV or less for typical OLED transport materials. Please understand that the term "approximately -3.0eV or less" means a value smaller than -3.0eV, such as -2.8eV, -2.5eV, -2.3eV, -2.1eV, or a value smaller than -2.0eV.

[0172] The electric n-dopant may be an organic compound such as those disclosed in EP1837926A1, WO07107306A1, or WO07107356A1.

[0173] Electrodopant is defined as being inherently non-luminescent.

[0174] The first electron transport layer and the second electron transport layer may be in direct contact with each other.

[0175] The electron transport laminate may consist of a first electron transport layer and a second electron transport layer.

[0176] The second electron transport layer may be in direct contact with the electron injection layer.

[0177] The electron injection layer may consist of several separate electron injection sublayers.

[0178] The electron injection layer may contain a metal, or an alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organoalkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate salt, or a mixture thereof.

[0179] The electron injection layer may consist of a metal, or alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organoalkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate salt, or a mixture thereof.

[0180] The compound of formula (II) may be defined as not being included in the electron injection layer. The compound of formula (I) may be defined as not being included in the electron injection layer. The compound of formula (III) may be defined as not being included in the electron injection layer.

[0181] The compound of formula (I), the compound of formula (II), and the compound of formula (III) may be different from each other and / or may not be contained in the electron injection layer.

[0182] The first electron transport laminate may be positioned between the first light-emitting layer and the first charge-generating layer. The second electron transport layer of the first electron transport laminate may be in direct contact with the first charge-generating layer.

[0183] The first electron transport layer and the second electron transport layer may be in direct contact with each other.

[0184] The electron transport laminate may consist of a first electron transport layer and a second electron transport layer.

[0185] The charge generation layer may include a p-type sublayer and an n-type sublayer, and the second electron transport layer may be in direct contact with the n-type sublayer.

[0186] The first charge generation layer may contain a metal, or an alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organoalkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0187] The charge generating layer may contain a metal, or alkali metal, metal salt, or alkaline earth metal salt and / or rare earth metal salt, or an organoalkali metal complex, or alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, metal borate, or a mixture thereof in its n-type sublayer.

[0188] The first charge generation layer may consist of a metal, or an alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organoalkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0189] The n-type sublayer of the first charge generation layer may consist of a metal, or an alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organoalkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0190] The organic light-emitting diode may further include an electron injection layer and a second electron transport laminate, the second electron transport laminate being in direct contact with the electron injection layer. The second electron transport laminate may contain the same compounds as the first laminate, i.e., compounds (I), (II), and (III) as defined herein, where each compound can be selected independently.

[0191] Compound (II) may be defined as not being included in the first charge generation layer. Compound (I) may be defined as not being included in the first charge generation layer. Compound (III) may be defined as not being included in the first charge generation layer.

[0192] Compound (I), compound (II), and compound (III) may be different from each other and / or may not be included in the first charge generation layer.

[0193] If the organic light-emitting device includes two or more electron transport laminates (i.e., other electron transport laminates in addition to the first electron transport laminate), all of the above characteristics relating to the first electron transport laminate can be applied independently to each electron transport laminate.

[0194] If the organic light-emitting device includes two or more charge generation layers (i.e., other charge generation layers in addition to the first charge generation layer), all of the above characteristics relating to the first charge generation layer can be applied independently to each charge generation layer.

[0195] The organic light-emitting diode may further include a substrate, which may be transparent or opaque.

[0196] [Exemplary Embodiments] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 C6~C 30 Aryl or C2~C 24 Selected independently from heteroaryls, Here, Ar 1 Each is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 1 Upper C6~C 12 Each aryl substituent, and Ar 1 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; A is C6~C 18 Selected independently of Aryl, Here, each of A is C6~C 12Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; X is C3~C 21 Heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Each aryl substituent, and C3-C3 on X 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; The molecular dipole moment of the compound of formula (I) is between 0D and 3.5D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 0, 1, or 2; Ar 2 C3~C 30 Heteroaryl and C6-C 42 Independently selected from the group consisting of aryls, Here, Ar 2 Each is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R10 These are independent, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, or partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 2 Upper C6~C 12 Each aryl substituent, and Ar 2 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; Z is C6~C 18 Selected independently of Aryl, Here, each of Z is C6~C 12 Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; G is selected such that the dipole moment of compound G-phenyl is between 2D and 6D; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0197] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 C6~C 30 Selected independently of Aryl, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A is C6~C 18 Selected independently from, Each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is C3~C 21 N-containing heteroaryl, C3~C 21 O-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is greater than or equal to 0D and greater than or equal to 3.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently either 1 or 2; k is independently 0, 1, or 2; Ar 2 C3~C 21 Heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is C6~C 18 Selected independently of Aryl, Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G includes dialkylphosphinyls, diarylphosphinyls, alkylarylphosphinyls, nitriles, benzonitriles, nicotinonitriles, amides, carbamides, and C2-C 42 Selected from the group consisting of heteroaryls; where G may include one or more substituents bonded to the base, and such one or more substituents are C6-C6 18 Aryl, C1~C 10 Alkyl, C2~C 14 Selected from the group consisting of heteroaryls; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0198] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 This is independently selected from phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa),

[0199] [ka]

[0200] During the ceremony, The asterisk symbol "*" indicates the bonding position where the base of equation (IIa) is attached to A; R 1 ~R 5 H, C6~C 12 Aryl and C3~C 10 Alternatively, independently selected from the group consisting of C4-C5 heteroaryls, Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was independently selected from phenylene, naphthylene, biphenylene, and terphenylene. Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is C3~C 21 N-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.5D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 C3~C 21 N-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is C2~C 25 Selected from the group consisting of heteroaryls; G may include one or more substituents bonded to the base, where the one or more substituents are C6-C6 12Aryl, C1-C6 alkyl, C2-C 11 Selected from the group consisting of heteroaryls; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0201] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 This is independently selected from the group consisting of phenyl, anthracenyl, fluorenyl, or the group of formula (IIb),

[0202] [ka]

[0203] During the ceremony, R 1 ~R 5 It is independently selected from H and phenyl, Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was independently selected from phenylene, naphthylene, biphenylene, and terphenylene. Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolinyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil; Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 These were independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolinyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil. Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is di-C1~C4-alkylphosphinyl, di-C6~C 10 -Arylphosphinyl, and C2~C 25 Selected from the group consisting of heteroaryls; where each G may contain one or more substituents bonded to the base, and these one or more substituents are C6-C6 10 Selected from the group consisting of aryl, C1-C4 alkyl, and C2-C5 heteroaryl; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0204] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 is the basis of equation (IIa),

[0205] [ka]

[0206] R 1 ~R 5 At least two of them are not H; Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was selected independently from phenylene and biphenylene; Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X may be substituted with one or two substituents independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil; Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 These were independently selected from the group consisting of dibenzoacridinyl, 1,3-diadinyl, 1,4-diadinyl, anthracenyl, triazinyl, phenatrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranil. Here, Ar 2Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, dihydro-benzimidazolone-yl, diphenyl-propane-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, phenylbenzoquinolinyl, phenylbenzimidazolone, pyridinyl, bipyridinyl, picolinyl, lutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyradinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl, and pyridinyl-imidazopyridinyl; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0207] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 is the basis of equation (IIa),

[0208] [ka]

[0209] R 1 ~R 5 At least two of them are not H, but R 1 ~R 5 At least two of these that are not H are in the ortho position relative to each other, and / or R 1 ~R 5 At least one of these that is not H is in the ortho position relative to the * position; Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was selected independently from phenylene and biphenylene; Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X was independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, and fluoranthenyl. Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n(II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 These were independently selected from the group consisting of dibenzoacridinyl, 1,3-diadinyl, 1,4-diadinyl, anthracenyl, triazinyl, phenatrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranil. Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridinyl, 2,2'-bipyridinyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinyl, and (pyridin-2-yl)imidazo[1,5-a]pyridinyl; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0210] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer comprises a compound selected from compounds A-1 to A-8 shown in Table 1; The second electron transport layer comprises a compound selected from compounds B-1 to B-25 shown in Table 3; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0211] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 C6~C 30 Aryl or C2~C 24 Selected independently from heteroaryls, Here, Ar 1 Each is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 1 Upper C6~C 12 Each aryl substituent, and Ar 1 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; A is C6~C 18 Selected independently of Aryl, Here, each of A is C6~C 12 Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; X is C3~C 21 Heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Each aryl substituent, and C3-C3 on X 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; The molecular dipole moment of the compound of formula (I) is between 0D and 3.5D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 0, 1, or 2; Ar 2 C3~C 30 Heteroaryl and C6-C 42 Independently selected from the group consisting of aryls, Here, Ar 2 Each is C6~C 12 Aryl, C3~C 11 Heteroaryls and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially fluorinated or perfluorinated C1-C6 alkyls, partially fluorinated or perfluorinated C1-C6 alkoxys, partially deuterated or hyperdeuterated C1-C6 alkyls, partially deuterated or hyperdeuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 These are independent, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, or partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, Ar 2 Upper C6~C 12 Each aryl substituent, and Ar 2 C3~C above 11 Each heteroaryl substituent may be substituted with a C1-C4 alkyl group or a halogen; Z is C6~C 18 Selected independently of Aryl, Here, each of Z is C6~C 12Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 ) may be substituted with one or two substituents independently selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 C6~C 12 Aryl, C3~C 12 Independently selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially fluorinated or perfluorinated C1-C6 alkyl, partially fluorinated or perfluorinated C1-C6 alkoxy, partially deuterated or hyperdeuterated C1-C6 alkyl, partially deuterated or hyperdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; G is selected such that the dipole moment of compound G-phenyl is between 2D and 6D; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0212] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 C6~C 30 Selected independently of Aryl, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A is C6~C 18 Selected independently from, Each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is C3~C 21 N-containing heteroaryl, C3~C 21 O-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is greater than or equal to 0D and greater than or equal to 3.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently either 1 or 2; k is independently 0, 1, or 2; Ar 2 C3~C 21Heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is C6~C 18 Selected independently of Aryl, Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G includes dialkylphosphinyls, diarylphosphinyls, alkylarylphosphinyls, nitriles, benzonitriles, nicotinonitriles, amides, carbamides, and C2-C 42 Selected from the group consisting of heteroaryls; where G may include one or more substituents bonded to the base, and such one or more substituents are C6-C6 18 Aryl, C1~C 10 Alkyl, C2~C 14 Selected from the group consisting of heteroaryls; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) comprises at least one heteroaromatic ring; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0213] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 This is independently selected from phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa),

[0214] [ka]

[0215] During the ceremony, The asterisk symbol "*" indicates the bonding position where the base of equation (IIa) is attached to A; R 1 ~R 5 H, C6~C 12 Aryl and C3~C 10 Alternatively, independently selected from the group consisting of C4-C5 heteroaryls, Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was independently selected from phenylene, naphthylene, biphenylene, and terphenylene. Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is C3~C 21 N-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.5D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 C3~C 21 N-containing heteroaryl and C6-C 24 Independently selected from the group consisting of aryls, Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is C2~C 25 Selected from the group consisting of heteroaryls; G may include one or more substituents bonded to the base, where the one or more substituents are C6-C6 12 Aryl, C1-C6 alkyl, C2-C 11 Selected from the group consisting of heteroaryls; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) comprises at least one heteroaromatic ring; The aromatic or heteroaromatic ring of compound (III) is a six-membered ring; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0216] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 This is independently selected from the group consisting of phenyl, anthracenyl, fluorenyl, or the group of formula (IIb),

[0217] [ka]

[0218] During the ceremony, R 1 ~R 5 It is independently selected from H and phenyl, Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was independently selected from phenylene, naphthylene, biphenylene, and terphenylene. Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X is independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolinyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil; Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 These were independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolinyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil. Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is di-C1~C4-alkylphosphinyl, di-C6~C 10 -Arylphosphinyl, and C2~C 25 Selected from the group consisting of heteroaryls; where each G may contain one or more substituents bonded to the base, and these one or more substituents are C6-C6 10 Selected from the group consisting of aryl, C1-C4 alkyl, and C2-C5 heteroaryl; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) comprises at least one heteroaromatic ring; The aromatic or heteroaromatic ring of compound (III) is a six-membered ring; The heteroaromatic ring of compound (III) is a nitrogen-containing heteroaromatic ring; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0219] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1is the basis of equation (IIa),

[0220] [ka]

[0221] R 1 ~R 5 At least two of them are not H; Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was selected independently from phenylene and biphenylene; Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X may be substituted with one or two substituents independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil; Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2These were independently selected from the group consisting of dibenzoacridinyl, 1,3-diadinyl, 1,4-diadinyl, anthracenyl, triazinyl, phenatrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranil. Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, dihydro-benzimidazolone-yl, diphenyl-propane-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, phenylbenzoquinolinyl, phenylbenzimidazolone, pyridinyl, bipyridinyl, picolinyl, lutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyradinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl, and pyridinyl-imidazopyridinyl; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) comprises at least one heteroaromatic ring; The aromatic or heteroaromatic ring of compound (III) is a six-membered ring; The heteroaromatic ring of compound (III) is a nitrogen-containing heteroaromatic ring; Compound (III) may contain at least one six-membered heteroaromatic ring containing 1 to 3 N atoms in each heteroaromatic ring; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0222] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer contains the compound of formula (I), (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar 1 is the basis of equation (IIa),

[0223] [ka]

[0224] R 1 ~R 5 At least two of them are not H, but R 1 ~R 5 At least two of these that are not H are in the ortho position relative to each other, and / or R 1 ~R 5 At least one of these that is not H is in the ortho position relative to the * position; Here, Ar 1 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl; A was selected independently from phenylene and biphenylene; Here, each of A may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; X was independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzoacridinyl, dibenzoacridinyl, and fluoranthenyl. Here, each of X may be substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenylyl; The molecular dipole moment of the compound of formula (I) is between 0D and 2.0D; The second electron transport layer contains the compound of formula (II), (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently either 1 or 2; Ar 2 These were independently selected from the group consisting of dibenzoacridinyl, 1,3-diadinyl, 1,4-diadinyl, anthracenyl, triazinyl, phenatrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranil. Here, Ar 2 Each may be substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenylyl, and optionally para-biphenylyl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene. Here, each Z may be substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl groups; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridinyl, 2,2'-bipyridinyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinyl, and (pyridin-2-yl)imidazo[1,5-a]pyridinyl; The second electron transport layer may further contain compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) comprises at least one heteroaromatic ring; The aromatic or heteroaromatic ring of compound (III) is a six-membered ring; The heteroaromatic ring of compound (III) is a nitrogen-containing heteroaromatic ring; Compound (III) may contain at least one six-membered heteroaromatic ring containing 1 to 3 N atoms in each heteroaromatic ring; Compound (III) contains two or more heteroaromatic rings; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0225] According to one embodiment, the laminate includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate. The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is positioned between the first light-emitting layer and the first charge-generating layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer comprises a compound selected from compounds A-1 to A-8 shown in Table 1; The second electron transport layer comprises a compound selected from compounds B-1 to B-25 shown in Table 3; The second electron transport layer further comprises a compound selected from compounds C-1 to C-6 shown in Table 4; The first electron transport layer and the second electron transport layer do not contain electrodopant. Organic light-emitting diodes are provided.

[0226] [Further layers] According to the present invention, the organic electronic device may include further layers in addition to the layers described above. Exemplary embodiments of each layer are described below.

[0227] 〔substrate〕 The substrate may be any substrate commonly used in the manufacture of electronic devices such as organic light-emitting diodes. If light is emitted through the substrate, the substrate may be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is emitted through the upper surface, the substrate may be both transparent and opaque, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0228] [Anode electrode] Either the first or second electrode included in the organic electronic device of the present invention may be an anode electrode. The anode electrode may be formed by vapor deposition or sputtering of the material used to form the anode electrode. The material used to form the anode electrode may be a high work function material to facilitate hole injection. The anode material may also be selected from low work function materials (i.e., aluminum). The anode electrode may be a transparent electrode or a reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO), can be used to form the anode electrode. The anode electrode may also be formed using a metal, typically silver (Ag), gold (Au), or a metal alloy. A transparent or translucent anode can facilitate light emission through the anode.

[0229] [Hole injection layer] Hole injection layers (HILs) can be formed on anode electrodes by methods such as vacuum deposition, spin coating, printing, casting, slot-die coating, and Langmuir-Blodgett (LB) deposition. When HILs are formed using vacuum deposition, the deposition conditions can vary depending on the compound used to form the HIL, as well as the desired structure and thermal properties of the HIL. However, generally, the conditions for vacuum deposition are a deposition temperature of 100°C to 500°C, and a temperature of 10°C. -8 ~10 -3 This can include a pressure of Torr (1 Torr is equal to 133.322 Pa) and an deposition rate of 0.1 to 10 nm / second.

[0230] When HILs are formed using spin coating or printing, the coating conditions may vary according to the compound used to form the HIL, as well as the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. The heat treatment removes the solvent after the coating has been carried out.

[0231] HIL can be formed from any compound commonly used to form HIL. Examples of compounds that can be used to form HIL include phthalocyanine compounds, such as copper phthalocyanine (CuPc), 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline) / poly(4-styrenesulfonate) (PANI / PSS).

[0232] HIL may contain or consist of a p-type dopant, which may be selected from, but not limited to, tetrafluorotetracyanoquinone dimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile, 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethanylylidene))tris(2,3,5,6-tetrafluorobenzonitrile), or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). HIL may be selected from hole transport matrix compounds doped with a p-type dopant. Typical examples of known doped hole transport materials include: copper phthalocyanine (CuPc) doped with tetrafluorotetracyanoquinone dimethane (F4TCNQ) with a LUMO level of approximately -5.2 eV and a HOMO level of approximately -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO=-5.2eV); α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; and α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile. The p-type dopant concentration can be selected from 1% to 20% by weight, more preferably from 3% to 10% by weight.

[0233] The thickness of the HIL can range from approximately 1 nm to approximately 100 nm, and for example, from approximately 1 nm to approximately 25 nm. Within this thickness range, the HIL can have excellent hole injection characteristics without a substantial penalty to the drive voltage.

[0234] [Hole transport layer] Hole transport layers (HTLs) can be formed on HTLs by methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When HTLs are formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for vacuum deposition or solution deposition may vary depending on the compound used to form the HTL.

[0235] HTLs can be formed from any compound commonly used to form HTLs. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, and are incorporated by reference. Examples of compounds that can be used to form HTLs include: carbazole derivatives such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds such as 4,4',4''-tris(N-carbazol)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and suppress the diffusion of excitons into the EML.

[0236] The thickness of the HTL may be in the range of approximately 5 nm to approximately 250 nm, preferably approximately 10 nm to approximately 200 nm, further approximately 20 nm to approximately 190 nm, further approximately 40 nm to approximately 180 nm, further approximately 60 nm to approximately 170 nm, further approximately 80 nm to approximately 160 nm, further approximately 100 nm to approximately 160 nm, and further approximately 120 nm to approximately 140 nm. A preferred thickness of the HTL may be 170 nm to 200 nm.

[0237] If the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without any substantial penalty to the drive voltage.

[0238] [Electron blocking layer] The function of an electron blocking layer (EBL) is to prevent electrons from moving from the light-emitting layer to the hole transport layer, thereby confining electrons to the light-emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, electron blocking layers contain triarylamine compounds. Triarylamine compounds can have a LUMO level closer to the vacuum level than the LUMO level of the hole transport layer. The electron blocking layer can have a HOMO level further away from the vacuum level than the HOMO level of the hole transport layer. The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0239] If the electron stopping layer has a high triplet level, the electron stopping layer can also be described as a triplet control layer.

[0240] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or blue light-emitting layer is used. This can increase the luminescence efficiency from the phosphorescent light-emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet level higher than the triplet level of the phosphorescent emitter in the adjacent light-emitting layer. Compounds suitable for the triplet control layer, particularly triarylamine compounds, are described in EP 2 722 908 A1.

[0241] [Emitting Layer (EML)] EMLs can be formed on HTLs by methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and LB deposition. When EMLs are formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for deposition and coating may vary depending on the compound used to form the EML.

[0242] The light-emitting layer may be specified as not containing the compounds of formula (I), formula (II), and / or compound (III).

[0243] The luminescent layer (EML) may be formed by a combination of a host and an emitter dopant. Examples of hosts include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distylyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2).

[0244] The emitter dopant may be a phosphorescent emitter or a fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0245] Examples of red emitter dopants include PtOEP, Ir(piq)3, and Btp2lr(acac), but are not limited to these. These compounds are phosphorescent emitters, but fluorescent red emitter dopants can also be used.

[0246] Examples of phosphorescent green emitter dopants include Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0247] Examples of phosphorescent blue emitter dopants include F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3, as well as ter-fluorene. 4,4'-Bis(4-diphenylamiostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0248] The emitter dopant content may be about 0.01 to about 50 parts by weight per 100 parts by weight of host. Alternatively, the light-emitting layer may be made of a light-emitting polymer. The EML can have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can have excellent light emission without a substantial penalty to the driving voltage.

[0249] [Hole Blocking Layer (HBL)] A hole blocking layer (HBL) can be formed on the EML using methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, or LB deposition to prevent hole diffusion into the ETL. If the EML contains a phosphorescent dopant, the HBL may also have triplet exciton blocking properties.

[0250] When HBLs are formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for deposition and coating may vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds for forming HBLs include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0251] HBLs can have a thickness of approximately 5 nm to 100 nm, for example, approximately 10 nm to 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking characteristics without a substantial penalty to the drive voltage.

[0252] [Electron transport layer (ETL)] The OLED according to the present invention comprises at least two electron transport layers (ETLs). At least two of the electron transport layers are a first electron transport layer and a second electron transport layer as defined herein. Furthermore, the OLED may include additional ETLs, which may or may not be as defined above. If the additional ETLs are not as defined above, their properties may be as follows:

[0253] According to various embodiments, the OLED may include an electron transport laminate comprising at least a first electron transport layer (ETL-1) containing a compound of formula (I) and at least a second electron transport layer (ETL-2) containing a compound of formula (II).

[0254] By appropriately tuning the energy levels of specific layers in the ETL, electron injection and transport can be controlled, and holes can be efficiently blocked. Therefore, OLEDs can have a long lifespan, improved performance, and stability.

[0255] [Electron injection layer (EIL)] The EIL can facilitate electron injection from the cathode to a second electron transport stack, and can be formed on the second electron transport stack, preferably directly on the second electron transport stack, preferably directly on the second electron transport layer of the second electron stack, and preferably in direct contact with the second electron transport layer of the second electron stack. Examples of materials for forming or included in the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The conditions for deposition and coating to form the EIL are similar to those for forming the HIL, although the conditions for deposition and coating may vary depending on the material used to form the EIL. The EIL may include an organic matrix material doped with an n-type dopant. The matrix material can be selected from materials conventionally used as matrix materials for electron transport layers.

[0256] An EIL can consist of several individual EIL sublayers. When an EIL consists of several individual EIL sublayers, the number of sublayers is preferably two. Each individual EIL sublayer can contain various materials for forming the EIL.

[0257] The thickness of the EIL can range from approximately 0.1 nm to approximately 10 nm, for example, from approximately 0.5 nm to approximately 9 nm. When the EIL thickness is within this range, the EIL can have good electron injection characteristics without a substantial penalty to the drive voltage.

[0258] The electron transport laminate of the present invention is not part of the electron injection layer.

[0259] [Cathode electrode] The cathode electrode is formed on the EIL, preferably directly on the EIL, and preferably in direct contact with the EIL, if an EIL is present. In the sense of the present invention, the cathode and EIL can be considered as a single functional part that enables the injection of electrons into the electron transport laminate. The cathode electrode may be formed from a metal, alloy, conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode can be formed from lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed from a transparent conductive oxide such as ITO or IZO.

[0260] The thickness of the cathode electrode may be in the range of approximately 5 nm to approximately 1000 nm, for example, in the range of approximately 10 nm to approximately 100 nm. When the thickness of the cathode electrode is in the range of approximately 5 nm to approximately 50 nm, the cathode electrode may be transparent or translucent, even if it is formed from a metal or metal alloy. A transparent or translucent cathode can facilitate light emission through the cathode.

[0261] It should be understood that the cathode electrode and electron injection layer are not part of the second electron transport layer or any other part of the electron transport laminate.

[0262] [Charge generation layer] The charge generation layer (CGL), i.e., the first CGL and any other CGL included in the OLED of the present invention, may include p-type CGLs and n-type CGLs. The intermediate layer may be disposed between the p-type layer and the n-type layer.

[0263] Typically, a charge generation layer (GCL) is a pn junction, where an n-type charge generation layer (electron generation layer, n-type CGL) and an a-type charge generation layer (hole generation layer, p-type CGL) are joined. The n-side of the pn junction generates electrons and injects them into the adjacent layer in the direction of the anode. Similarly, the p-side of the pn junction generates holes and injects them into the adjacent layer in the direction of the cathode.

[0264] The charge generation layer is used in a tandem OLED (such as the one disclosed herein) which includes two or more light-emitting layers between the cathode and the anode. In a tandem OLED with two light-emitting layers, the n-type charge generation layer supplies electrons to a first light-emitting layer located near the anode, while the hole generation layer supplies holes to a second light-emitting layer located between the first light-emitting layer and the cathode.

[0265] Suitable matrix materials for the hole generation layer may be materials conventionally used as hole injection matrix materials and / or hole transport matrix materials. Furthermore, conventional materials can be used for the p-type dopant used in the hole generation layer. For example, the p-type dopant may be one selected from the group consisting of tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, radialene derivatives, iodine, FeCl3, FeF3, and SbCl5. The host may be one selected from the group consisting of N,N'-di(naphthalene-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB). The p-type charge generation layer may consist of CNHAT.

[0266] The n-type charge generation layer may be a layer of undiluted (neat) n-type dopant, as an example of an electrically positive metal, or it may consist of an organic matrix material doped with an n-type dopant. In one embodiment, the n-type dopant may be an alkali metal, alkali metal compound, alkaline earth metal, alkaline earth metal compound, transition metal, transition metal compound, or rare earth metal. In another embodiment, the metal may be one selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant may be one selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. Suitable matrix materials for the n-type charge generation layer may be materials conventionally used as matrix materials for electron injection layers or electron transport layers. The matrix material may be one selected from the group consisting of, for example, compound E, triazine compounds such as bipyridyl and terpyridyl compounds, N-containing heterocyclic compounds such as phenatroline compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminum, benzazole derivatives, and silole derivatives.

[0267] The hole generation layer may be positioned in direct contact with the n-type charge generation layer.

[0268] The electron transport laminate of the present invention is not part of the charge generation layer.

[0269] [Organic Light-Emitting Diode (OLED)] According to various embodiments of the present invention, an OLED layer may be provided which is disposed between the above-mentioned layers, on the substrate, or on the upper electrode.

[0270] According to one aspect of the present invention, an organic light-emitting diode is provided, comprising a substrate, an anode, a first hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first arbitrary hole blocking layer, a first electron transport laminate, an n-type charge generation layer, a hole generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second arbitrary hole blocking layer, a second electron transport laminate, a second electron injection layer, and a cathode.

[0271] According to one aspect of the present invention, an organic light-emitting diode is provided, comprising a substrate, an anode, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, and a second electron transport layer; a second electron transport laminate comprising a first charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a third electron transport layer (= the first electron transport layer of the second laminate), and a fourth electron transport layer (= the second electron transport layer of the second laminate); a third electron transport laminate comprising a second charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a fifth electron transport layer (= the first electron transport layer of the third laminate), and a sixth electron transport layer (= the second electron transport layer of the third laminate); an electron injection layer; and a cathode.

[0272] According to one embodiment, the OLED may have a layered structure in which a substrate is arranged adjacent to the anode electrode, the anode electrode is arranged adjacent to a first hole injection layer, the first hole injection layer is arranged adjacent to a first hole transport layer, the first hole transport layer is arranged adjacent to a first electron blocking layer, the first electron blocking layer is arranged adjacent to a first light-emitting layer, the first light-emitting layer is arranged adjacent to a first electron transport laminate including a first electron transport layer and a second electron transport layer, the first electron transport laminate is arranged adjacent to an electron injection layer, and the electron injection layer is arranged adjacent to the cathode electrode.

[0273] For example, the OLED shown in Figure 1 may be formed by a process in which an anode 120, a first hole injection layer 130, a first hole transport layer 140, a first electron blocking layer 145, a first light-emitting layer 150, a first electron transport laminate 160, an n-type charge generation layer 185, a hole generation layer 135, a second hole transport layer 141, a second electron blocking layer 146, a second light-emitting layer 151, a second electron transport laminate 165, a second electron injection layer 181, and an anode 190 are continuously formed on a substrate 110 in this order.

[0274] For example, the OLED shown in Figure 2 has an anode 120 on which a hole injection layer 130, a first hole transport layer 140, a first electron blocking layer 145, a first light-emitting layer 150, a first electron transport layer 161 and a second electron transport layer 162 are included, a first charge generation layer 184 including n-type CGL sublayers 184a and p-type CGL sublayers 184b, a second hole transport layer 141, a second electron blocking layer 146, a second light-emitting layer 151, a third electron transport layer (= first electron transport layer of the second laminate) 166 and a fourth electron transport layer (= second stack) The following may be formed by a process in which a second electron transport laminate 165 including a second electron transport layer 167 of the laminate, a second charge generation layer 186 including n-type CGL sublayers 186a and p-type CGL sublayers 186b, a third hole transport layer 142, a third electron blocking layer 147, a third light-emitting layer 152, a third electron transport laminate 168 including a fifth electron transport layer (= first electron transport layer of the third laminate) 163 and a sixth electron transport layer (= second electron transport layer of the third laminate) 164, an electron injection layer 181, and a cathode 190 are formed in this order in a continuous manner.

[0275] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method employing the following: - At least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0276] Suitable methods for vapor deposition include: - Vapor deposition by vacuum thermal evaporation; - Deposition by solution treatment (preferably selected from spin coating, printing, and casting); and / or -Slot-die coating.

[0277] If one or more of the second electron transport layers contain compound (III) and the compound of formula (II), the two compounds may be deposited by co-deposition from two separate deposition sources, or as a premix for a single source.

[0278] According to various embodiments of the present invention, the method may further include forming an emissive layer and at least one layer on the anode electrode, wherein the formation of at least one layer is selected from the group consisting of forming a hole injection layer, a hole transport layer, or a hole blocking layer between the anode electrode and the first electron transport layer.

[0279] According to various embodiments of the present invention, the method may further include a step for forming an organic light-emitting diode (OLED), where, -A first anode electrode is formed on the substrate, - An emissive layer is formed on the first anode electrode. - An electron transport laminate is formed on the light-emitting layer, and a charge generation layer is formed on the electron transport laminate, -Finally, the cathode electrode is formed, -Optionally, a hole injection layer, a hole transport layer, and a hole blocking layer are formed between the first anode electrode and the light-emitting layer in that order. - A charge generation layer is formed between the electron transport laminate and the cathode electrode.

[0280] According to various embodiments, an OLED can have the following layered structure, where the layers are in the following order: Anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, any hole blocking layer, electron transport laminate, n-type CGL, p-type CGL, hole transport layer, electron blocking layer, light-emitting layer, any hole blocking layer, electron transport laminate, n-type CGL, p-type CGL, hole transport layer, electron blocking layer, light-emitting layer, any hole blocking layer, electron transport laminate, electron injection layer, and cathode.

[0281] According to another aspect of the present invention, an electronic device is provided which includes at least one organic light-emitting device as described throughout this application, preferably the electronic device includes an organic light-emitting diode as described throughout this application. More preferably the electronic device is a display device or a light-emitting device.

[0282] In one embodiment, the organic electronic device according to the present invention may further include a layer containing a radialene compound and / or a quinodimethane compound.

[0283] In one embodiment, the radialene compound and / or quinodimethane compound may be substituted with one or more halogen atoms and / or one or more electron-withdrawing groups. The electron-withdrawing groups can be selected from nitrile groups, alkyl halides, alkyl perhalides, or alkyl perfluoroides. Other examples of electron-withdrawing groups may be acyl groups, sulfonyl groups, or phosphoryl groups.

[0284] Alternatively, the acyl group, sulfonyl group and / or phosphoryl group may include halogenated and / or perhalated hydrocarbils. In one embodiment, the perhalated hydrocarbil may be a perfluorohydrocarbil. Examples of perfluorohydrocarbils may be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, and perfluorotolyl; examples of sulfonyl groups containing halogenated hydrocarbils may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, and the like.

[0285] In one embodiment, the radialene and / or quinodimethane compound may be included in the hole injection layer, the hole transport layer and / or the hole generation layer.

[0286] In one embodiment, the radialene compound may have formula (XX), and / or the quinodimethane compound may have formula (XXIa) or (XXIb):

[0287] [ka]

[0288] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 15 , R 16 , R 20 , R 21 R is selected independently of the electron-withdrawing groups mentioned above. 9 , R 10 , R 13 , R 14 , R 17 , R 18 , R19 , R 22 , R 23 and R 24 (The element is independently selected from H, halogens, and the electron-withdrawing groups mentioned above.)

[0289] The embodiments will be described in more detail below with reference to examples. However, the present invention is not limited to the following embodiments. Here, the exemplary embodiments will be described in detail.

[0290] [General definition] In this specification, unless otherwise provided, “alkyl group” may refer to an aliphatic hydrocarbon group. An alkyl group may refer to a “saturated alkyl group” that does not contain double or triple bonds. As used herein, the term “alkyl group” encompasses linear, branched, and cyclic alkyl groups. For example, C3-alkyl groups may be selected from n-propyl and isopropyl groups. Similarly, C4-alkyl groups encompass n-butyl, sec-butyl, and t-butyl groups. Similarly, C6-alkyl groups encompass n-hexyl and cyclohexyl groups.

[0291] Where used herein, unless otherwise explicitly stated, the asterisk symbol "*" indicates a binding position where a correspondingly marked portion joins another portion.

[0292] C n The subscript n in the middle refers to the total number of carbon atoms in each alkyl group, arylene group, heteroarylene group, or aryl group.

[0293] As used herein, the terms “aryl” or “arirene” encompass condensed aromatics such as phenyl (C6-aryl), naphthalene, anthracene, phenanthrene, and tetracene. Biphenyls and oligophenyls or polyphenyls, such as terphenyls, phenyl-substituted biphenyls, and phenyl-substituted terphenyls (e.g., tetraphenylbenzol group), are further encompassed. “Arirene” and “heteroarirene” each refer to a group to which two further parts are bonded. In this specification, the terms “aryl group” or “arirene group” may refer to a group comprising at least one hydrocarbon aromatic moiety, where all elements of the hydrocarbon aromatic moiety may have p-orbitals forming conjugation (e.g., phenyl group, naphthyl group, anthracenyl group, phenantrenyl group, pyrinyl group, fluorenyl group, etc.). Spiro compounds (e.g., 9,9'-spiroby[9H-fluorene]yl) in which two aromatic moieties are connected to each other via a spiro atom are further encompassed. Aryl or arylene groups may include monocyclic or fused polycyclic (i.e., bonded) functional groups that share adjacent pairs of carbon atoms.

[0294] As used herein, the term “heteroaryl” refers to an aryl group in which at least one carbon atom is substituted with a heteroatom. The term “heteroaryl” may also refer to an aromatic heteroring having at least one heteroatom, where all elements of the hydrocarbon heteroaromatic moiety may have p orbitals that form conjugates. The heteroatom can be selected from N, O, S, B, Si, P, Se, preferably N, O, and S. A heteroarylene ring can contain at least one to three heteroatoms. Preferably, a heteroarylene ring can contain at least one to three heteroatoms independently selected from N, S, and / or O. As with “aryl” / “arylene”, the term “heteroaryl” includes, for example, spiro compounds in which two aromatic moieties are bonded to each other (e.g., spiro[fluorene-9,9'-xanthene]). Further exemplary heteroaryl groups include diazine, triazine, dibenzofuran, dibenzothiofuran, acridine, benzoacridine, and dibenzoacridine.

[0295] As used herein, the term "alkenyl" refers to a group containing a carbon-carbon double bond (-CR). 1 =CR 2 R 3 It refers to.

[0296] As used herein, the term "perhalogenation" refers to a hydrocarbyl group in which all of its hydrogen atoms are replaced by halogen (F, Cl, Br, I) atoms.

[0297] As used herein, the term "alkoxy" refers to a structural fragment of the formula -OR (where R is a hydrocarbyl, preferably an alkyl or cycloalkyl).

[0298] As used herein, the term "thioalkyl" refers to a structural fragment of the formula -SR (where R is hydrocarbyl, preferably alkyl or cycloalkyl).

[0299] C n- In heteroaryl groups, the subscript n simply refers to the number of carbon atoms excluding the heteroatom. In this context, it is clear that C3 heteroarylene groups are aromatic compounds containing three carbon atoms (such as pyrazoles, imidazoles, oxazoles, and thiazoles).

[0300] As used herein, the term "heteroaryl" includes pyridine, quinoline, benzoquinoline, quinazoline, benzoquinazoline, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, benzo[4,5]thieno[3,2-d]pyrimidine, carbazole, xanthene, phenoxazine, benzoacridine, dibenzoacridine, and the like.

[0301] In this specification, the term "single bond" refers to a direct bond.

[0302] As used herein, the term "fluorinated" refers to a hydrocarbon group in which at least one of the hydrogen atoms in the hydrocarbon group is replaced by a fluorine atom. A fluorinated group in which all of the hydrogen atoms are replaced by fluorine atoms is called a perfluorinated group and is specifically referred to as "fluorinated".

[0303] In relation to the present invention, if one of the hydrogen atoms contained in a group is replaced by another group, that group is "substituted" by the other group (where the other group is a substituent).

[0304] In relation to the present invention, the expression “between” with respect to one layer located between two other layers does not preclude the presence of a further layer that may be placed between that layer and one of the other two layers. In relation to the present invention, the expression “in direct contact” with respect to two layers that are in direct contact with each other means that no further layer is placed between those two layers. One layer deposited on top of another layer is considered to be in direct contact with that layer.

[0305] The term "sandwiched and in contact" refers to an arrangement of three layers in which the middle layer is in direct contact with two adjacent layers.

[0306] Regarding the electron transport laminate of the present invention, the compound described in the experimental section is most preferred.

[0307] A light-emitting device can be any of the devices used for illumination, irradiation, signaling, or projection. They are classified accordingly as illumination devices, irradiation devices, signaling devices, and projection devices. A light-emitting device typically consists of a light source, a device that transmits the radiant beam into space in a desired direction, and a housing that joins the components into a single device and protects the light source and light transmission system from damage and ambient influences.

[0308] In another embodiment, the organic electroluminescent apparatus according to the present invention includes two or more light-emitting layers. An OLED including two or more light-emitting layers is also described as a tandem OLED or a stacked OLED.

[0309] The organic electroluminescent device (OLED) may be a bottom-emission device or a top-emission device. The organic electroluminescent device (OLED) may emit light through a transparent anode or through a transparent cathode.

[0310] Another embodiment relates to an apparatus that includes at least one organic electroluminescent device (OLED).

[0311] Devices containing organic light-emitting diodes include, for example, display panels or light-emitting panels.

[0312] In the present invention, the terms defined below shall have the same meaning unless different definitions are given in the claims or elsewhere in this specification.

[0313] In the context of this specification, the terms “different” or “differs” in relation to matrix materials mean that the matrix materials differ in their structural formula.

[0314] The terms "OLED" and "organic light-emitting diode" are used simultaneously and have the same meaning. As used herein, the term "organic electroluminescent device" may include both organic light-emitting diodes and organic light-emitting transistors (OLETs).

[0315] As used herein, "weight percent," "wt.-%," "percent by weight," "% by weight," and their variations refer to the weight of each component, substance, or active material in each electron transport layer divided by the total weight of each electron transport layer and multiplied by 100. It is understood that the total weight percent of all components, substances, and active materials in each electron transport layer and electron injection layer should not exceed 100 wt%.

[0316] As used herein, “volume percent,” “vol.-%,” “percent by volume,” “% by volume,” and their variations refer to the volume of each component, substance, or active material in each electron transport layer divided by the total volume of each electron transport layer and multiplied by 100. It is understood that the total volume percentage of all components, substances, and active materials in the cathode layer should not exceed 100 vol%.

[0317] In this specification, all numerical values, whether expressly indicated or not, are assumed to be modified by the term "approximately." As used herein, the term "approximately" refers to possible variations in quantity. Whether modified by the term "approximately" or not, the claims include equivalents to those quantities.

[0318] As used herein and in the appended claims, the singular forms "a," "an," and "the" refer to multiple subjects unless the content clearly indicates otherwise.

[0319] The terms "free of," "does not contain," and "dose not comprised" do not exclude impurities. Impurities do not have a technical impact on the objectives achieved by this invention.

[0320] In the context of this specification, the terms “essentially non-luminescent” or “non-luminescent” mean that the contribution of the compound or layer to the visible emission spectrum from the apparatus is less than 10%, preferably less than 5%, of the visible emission spectrum. The visible emission spectrum is an emission spectrum having wavelengths between approximately 380 nm and approximately 780 nm.

[0321] Preferably, the organic semiconductor layer containing the compound of formula (I) is essentially non-luminescent or non-luminescent.

[0322] The operating voltage, also known as U, is 10 milliamperes per square centimeter (mA / cm²). 2 It is measured at the bolt (V) in ).

[0323] Candela / ampere efficiency, also known as cd / A efficiency, is 10 milliamperes per square centimeter (mA / cm²). 2 It is measured in candela / ampere at )

[0324] External quantum efficiency, also known as EQE, is measured in percentage (%).

[0325] The color space is described by coordinates CIE-x and CIE-y (International Commission on Illumination 1931). For blue light emission, CIE-y is particularly important. A smaller CIE-y indicates a deeper blue color. Efficiency values ​​are compared using the same CIE-y.

[0326] The highest occupied molecular orbital, also known as the HOMO, and the lowest unoccupied molecular orbital, also known as the LUMO, are measured in electron volts (eV).

[0327] The terms "OLED," "organic light-emitting diode," "organic light-emitting device," "organic photoelectron device," and "organic light-emitting diode" are used simultaneously and have the same meaning.

[0328] The terms "life-span" and "lifetime" are used simultaneously and have the same meaning.

[0329] The anode and cathode can be described as an anode electrode / cathode electrode, an anode electrode / cathode electrode, or an anode electrode layer / cathode electrode layer.

[0330] Room temperature, also known as ambient temperature, is 23°C.

[0331] [Brief explanation of the drawing] These and / or other aspects and effects of the present invention will become apparent and more readily understood from the following description of exemplary embodiments in conjunction with the accompanying drawings: Figure 1 is a schematic cross-sectional view of a multi-layer organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; Figure 2 is a schematic cross-sectional view of a multi-emissive layer OLED according to an exemplary embodiment of the present invention.

[0332] [Detailed explanation] Hereinafter, exemplary embodiments of the present invention will be described in detail, examples of which are shown in the accompanying drawings. Hereinafter, similar reference numerals refer to similar elements throughout. Illustrative embodiments of the present invention will be described below with reference to the drawings.

[0333] Where it is stated in this specification that a first element is formed or positioned "on" or "onto" a second element, the first element may be positioned directly on the second element, or one or more other elements may be positioned between them. Where it is stated that a first element is formed or positioned "directly on" or "directly onto" a second element, no other elements are positioned between them.

[0334] Figure 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 200 according to an exemplary embodiment of the present invention. The OLED 200 comprises a substrate 110, an anode 120, a first hole injection layer (HIL-1) 130, a first hole transport layer (HTL-1) 140, a first electron blocking layer (EBL-1) 145, a first light-emitting layer (EML-1) 150, a first electron transport laminate (ETL-1) 160 including a first electron transport layer 161 and a second electron transport layer 162 of the first laminate, an n-type charge generation layer (n-type CGL) 185, and a hole generation layer (p The device includes a p-type charge generation layer (p-type GCL) 135, a second hole transport layer (HTL-2) 141, a second electron blocking layer (EBL-2) 146, a second light-emitting layer (EML-2) 151, a second electron transport laminate (ETL-2) 165 containing a third electron transport layer (= first electron transport layer of the second laminate) 166 and a fourth electron transport layer (= second electron transport layer of the second laminate) 167, an electron injection layer (EIL) 181, and a cathode 190.

[0335] Referring to Figure 2, the OLED200 consists of an anode 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL-1) 140, a first electron blocking layer (EBL-1) 145, a first light-emitting layer (EML-1) 150, a first electron transport laminate (ETL-1) 160 including a first electron transport layer 161 and a second electron transport layer 162, a first charge generation layer (CGL-1) 184, a second hole transport layer (HTL-2) 141, a second electron blocking layer (EBL-2) 146, a second light-emitting layer (EML-2) 151, and a third electron transport layer (= the first electron transport layer of the second laminate). The OLED includes a second electron transport laminate (ETL-2) 165 containing a 166 and a fourth electron transport layer (= second electron transport layer of the second laminate) 167, a second charge generation layer (CGL-2) 186, a third hole transport layer (HTL-3), a third electron blocking layer (EBL-3) 147, a third light-emitting layer (EML-3) 152, a third electron transport laminate (ETL-3) 168 containing a fifth electron transport layer (= first electron transport layer of the third laminate) 163 and a sixth electron transport layer (= second electron transport layer of the third laminate) 164, an electron injection layer (EIL) 181, and a cathode 190. The OLED shown in Figure 2 has a first light-emitting section A, a second light-emitting section B, and a third light-emitting section C.

[0336] Although not shown in Figures 1 and 2, a sealing layer may be further formed on the cathode electrode 190 to encapsulate the OLED 200. Various other modifications may also be applied.

[0337] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of one or more exemplary embodiments of the present invention.

[0338] [Detailed explanation] [Dipole moment] Dipole moment of a molecule containing a nitrogen atom

[0339]

number

[0340] This is given by the following formula:

[0341]

number

[0342] During the ceremony,

[0343]

number

[0344] This represents the partial charge and position of atom i in the molecule.

[0345] The dipole moment is determined by the semi-empirical molecular orbital method.

[0346] As implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), 6-31G in the gas phase. * The geometric shape of the molecular structure is optimized by applying the hybrid function B3LYP, which has a ground system. If two or more conformations are feasible, the conformation with the lowest total energy is selected to determine the bond length of the molecule.

[0347] [Calculated values ​​of HOMO and LUMO] HOMO and LUMO are calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized molecular structure and HOMO and LUMO energy levels are calculated in the gas phase from 6–31G. *This is determined by applying the hybrid function B3LYP, which has a base set. If two or more conformations are feasible, the conformation with the lowest total energy is selected.

[0348] [Measurement of OLED performance] To evaluate the performance of the OLED device, the current efficiency is measured at 20°C. The current-voltage characteristics are determined by supplying a voltage in V and measuring the current flowing through the device under test in mA using a Keithley 2635 source measurement unit. The voltage applied to the device varies in 0.1V increments within the range of 0V to 10V. Similarly, the luminance-voltage characteristics and CIE coordinates are measured for each voltage value using an Instrument Systems CAS-140CT array analyzer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) in cd / m². 2 It is determined by measuring the brightness. 10mA / cm 2 The cd / A efficiency is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[0349] Where applicable, the device life LT is under ambient conditions (20°C) and 30 mA / cm². 2 Then, measurements can be taken using the Keithley 2400 source meter and recorded in time units.

[0350] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time it takes for the brightness of the device to decrease to 97% of its initial value.

[0351] The increase in the operating voltage ΔU is used as a measure of the operating voltage stability of the device. This increase is determined during LT measurement by subtracting the operating voltage at the start of device operation from the operating voltage after 50 hours.

[0352] ΔU = [U(50h) - U(0h)] The smaller the value of ΔU, the better the operating voltage stability.

[0353] [General procedures for OLED manufacturing] As a top-emission OLED device, a substrate with dimensions of 150mm x 150mm x 0.7mm was ultrasonically cleaned in a spin-cleaning dryer with a 2% aqueous solution of Deconex FPD 211 for 7 minutes, then with pure water for 5 minutes, and dried for 15 minutes. Subsequently, with Ag as the anode, 10 -5 ~10 -7 The deposition was carried out at a pressure of mbar.

[0354] Next, HT-1 and D-1 were vacuum co-deposited onto the anode to form a High-Intensity Layer (HIL). Then, HT-1 was vacuum-deposited onto the HIL to form a High-Intensity Layer (HTL). Finally, HT-2 was vacuum-deposited onto the HTL to form an Electron Blocking Layer (EBL).

[0355] Subsequently, a first light-emitting layer was formed on the EBL by co-deposition of host-1 and emitter-1.

[0356] Next, the compound of formula (I) was vacuum deposited onto the light-emitting layer to form a first electron transport layer. Then, as Examples OLED-1 to OLED-4, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II). As a comparative OLED example, a second electron transport layer was formed on the first electron transport layer by depositing compound C-3.

[0357] In Examples OLED-5 to OLED-15, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II) and the premix compound of compound (III).

[0358] Next, n-type CGL was formed on the second electron transport layer by co-depositing compound E and lithium.

[0359] Next, HT-1 and D-1 were co-deposited onto the n-type CGL using vacuum deposition to form a p-type CGL.

[0360] Next, HT-1 was vacuum-deposited onto p-type CGL to form an HTL. Then, HT-2 was vacuum-deposited onto the HTL to form an EBL.

[0361] Subsequently, a second light-emitting layer was formed on the EBL by co-deposition of host-1 and emitter-1.

[0362] Next, the compound of formula (I) was vacuum deposited onto the light-emitting layer to form a first electron transport layer. Then, as Examples OLED-1 to OLED-4, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II). As a comparative OLED example, a second electron transport layer was formed on the first electron transport layer by depositing compound C-3.

[0363] In Examples OLED-5 to OLED-15, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II) and the premix compound of compound (III).

[0364] Next, n-CGL was formed on the second electron transport layer by co-depositing compound E and lithium.

[0365] Next, HT-1 and D-1 were co-deposited onto the n-type CGL using vacuum deposition to form a p-type CGL.

[0366] Next, HT-1 was vacuum-deposited onto the HIL to form an HTL. Then, HT-2 was vacuum-deposited onto the HTL to form an electron blocking layer (EBL).

[0367] Subsequently, a third light-emitting layer was formed on the EBL by co-deposition of host-1 and emitter-1.

[0368] Next, the compound of formula (I) was vacuum deposited onto the light-emitting layer to form a first electron transport layer. Then, as Examples OLED-1 to OLED-4, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II). As a comparative OLED example, a second electron transport layer was formed on the first electron transport layer by depositing compound C-3.

[0369] In Examples OLED-5 to OLED-15, a second electron transport layer was formed on the first electron transport layer by depositing the compound of formula (II) and the premix compound of compound (III).

[0370] Next, an electron injection layer is formed as a double layer on the electron transport layer by first depositing LiQ and then Yb.

[0371] Next, Ag:Mg, 10 -7 The cathode was formed by evaporation at a rate of 0.01 to 1 Å / s in mbar.

[0372] The HT-3 cap layer was formed on the cathode.

[0373] The details of the laminate in a top-emission OLED device are shown below. A slash " / " separates individual layers. Layer thicknesses are indicated in square brackets [...], and mixing ratios are indicated in parentheses (...) in weight percent: Details of the laminate used in the OLED device example in Table 6: Ag[100nm] / HT-1:D-1(weight% 92:8)[10nm] / HT-1[24nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / compound of formula (I)[5nm] / compound of formula (II) or C-3[25nm] / E:Li(weight% 99:1)[15nm] / HT-1:D-1(weight% 90:10)[10nm] / HT-1[36nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / compound of formula (I)[5nm] / compound of formula (II) or C-3[25nm] / E:Li(weight% 99:1)[15nm] / HT-1:D-1(weight% 90:10)[10nm] / HT-1[57nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / compound of formula (I)[5nm] / compound of formula (II) or C-3[30nm] / LiQ[1nm] / Yb[2nm] / Ag:Mg(weight% 90:10)[13nm] / HT-3[65nm].

[0374] Details of the laminate used in the OLED device example in Table 7: Ag[100nm] / HT-1:D-1(weight% 92:8)[10nm] / HT-1[24nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / Compound of formula (I)[5nm] / Compound of formula (II):Compound of formula (III)(weight% 30:70)[25nm] / E:Li(weight% 99:1)[15nm] / HT-1:D-1(weight% 90:10)[10nm] / HT-1[36nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / Compound of formula (I)[5nm] / Compound of formula (II):Compound of formula (III)(weight% 30:70)[25nm] / E:Li(weight% 99:1)[15nm] / HT-1:D-1(weight% 90:10)[10nm] / HT-1[57nm] / HT-2[5nm] / H09:BD200(weight% 97:3)[20nm] / compound of formula (I)[5nm] / compound of formula (II):compound of formula (III)(weight% 30:70)[30nm] / LiQ[1nm] / Yb[2nm] / Ag:Mg(weight% 90:10)[13nm] / HT-3[65nm].

[0375] [Table 6]

[0376] [Table 7]

[0377] [Table 8]

[0378] Examples 8, 9, and 10 demonstrate that when compound (III) is used in the second electron transport layer, the cd / A efficiency is further increased at lower voltages.

[0379] The features described above and disclosed in the dependent claims may, individually and in any combination thereof, be materials for realizing the aspects of the invention made in the independent claims in various forms. [Brief explanation of the drawing]

[0380] [Figure 1] Figure 1 is a schematic cross-sectional view of a multi-layer organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. [Figure 2] Figure 2 is a schematic cross-sectional view of a multi-emissive layer OLED according to an exemplary embodiment of the present invention.

Claims

1. It includes an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron-transport laminate, The first charge generation layer is positioned between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate is disposed between the first light-emitting layer and the second light-emitting layer; The first electron transport laminate includes a first electron transport layer and a second electron transport layer; The first electron transport layer comprises the compound of formula (I), (Ar １ -A ｃ ) ａ -X ｂ (I); a and b are independently 1 or 2; c is independently either 0 or 1; Ar １ is selected independently from C ６ to C ６０ aryl or C ２ to C ４２ heteroaryl, Here, Ar １ Each is C ６ ~C １２ Ariel, C ３ ~C １１ Heteroaryl and C １ ~C ６ Alkyl, D, C １ ~C ６ Alkoxy, C ３ ~C ６ Branched alkyl, C ３ ~C ６ Cyclic alkyl, C ３ ~C ６ Branched alkoxy, C ３ ~C ６ Cyclic alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R) １０ ) ２ It may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, and R １０ C ６ ~C １２ Ariel, C ３ ~C １２ Heteroaryl, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Selected independently of alkoxy; Here, Ar １ Upper C ６ ~C １２ Each aryl substituent, and Ar １ Upper C ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ They may be substituted with alkyl or halogen; A is C ６ ~C ３０ Selected independently of Aryl, Here, each of A is C ６ ~C １２ aryl and C １ ~C ６ alkyl, D, C １ ~C ６ alkoxy, C ３ ~C ６ branched alkyl, C ３ ~C ６ cyclic alkyl, C ３ ~C ６ branched alkoxy, C ３ ~C ６ cyclic alkoxy, partially fluorinated or perfluorinated C １ ~C ６ alkyl, partially fluorinated or perfluorinated C １ ~C ６ alkoxy, partially deuterated or perdeuterated C １ ~C ６ alkyl, partially deuterated or perdeuterated C １ ~C ６ alkoxy, halogen, CN or PY(R １０ ) ２ and may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, and R １０ is C ６ ~C １２ aryl, C ３ ~C １２ heteroaryl, C １ ~C ６ alkyl, C １ ~C ６ alkoxy, partially fluorinated or perfluorinated C １ ~C ６ alkyl, partially fluorinated or perfluorinated C １ ~C ６ alkoxy, partially deuterated or perdeuterated C １ ~C ６ alkyl, partially deuterated or perdeuterated C １ ~C ６ is independently selected from alkoxy; Here, C on A ６ ~C １２ Each aryl substituent is C １ ~C ４ They may be substituted with alkyl or halogen; X is C ２ ~C ４２ Heteroaryl and C ６ ~C ６０ Independently selected from the group consisting of aryls, Here, each X is C ６ ~C １２ Ariel, C ３ ~C １１ Heteroaryl and C １ ~C ６ Alkyl, D, C １ ~C ６ Alkoxy, C ３ ~C ６ Branched alkyl, C ３ ~C ６ Cyclic alkyl, C ３ ~C ６ Branched alkoxy, C ３ ~C ６ Cyclic alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R) １０ ) ２ It may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, and R １０ C ６ ~C １２ Ariel, C ３ ~C １２ Heteroaryl, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Selected independently of alkoxy; Here, C on X ６ ~C １２ Each aryl substituent, and C on X ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ They may be substituted with alkyl or halogen; The molecular dipole moment of the compound in formula (I) is 0D or greater and 4D or less; The second electron transport layer comprises the compound of formula (II), (2r ２ ) ) ｍ -() ｋ -1) ｎ (99); m and n are independently 1 or 2; k is independently 0, 1, or 2; Ar ２ C ２ ~C ４２ Heteroaryl and C ６ ~C ６０ Independently selected from the group consisting of aryls, Here, Ar ２ Each is C ６ ~C １２ Ariel, C ３ ~C １１ Heteroaryl and C １ ~C ６ Alkyl, D, C １ ~C ６ Alkoxy, C ３ ~C ６ Branched alkyl, C ３ ~C ６ Cyclic alkyl, C ３ ~C ６ Branched alkoxy, C ３ ~C ６ Cyclic alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R) １０ ) ２ It may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, and R １０ C is independent ６ ~C １２ Ariel, C ３ ~C １２ Heteroaryl, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Selected from alkoxy; Here, Ar ２ Upper C ６ ~C １２ Each aryl substituent, and Ar ２ Upper C ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ They may be substituted with alkyl or halogen; Z is C ６ ~C ３０ Selected independently of Aryl, Here, each Z is C ６ ~C １２ Aryl and C １ ~C ６ Alkyl, D, C １ ~C ６ Alkoxy, C ３ ~C ６ Branched alkyl, C ３ ~C ６ Cyclic alkyl, C ３ ~C ６ Branched alkoxy, C ３ ~C ６ Cyclic alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R) １０ ) ２ It may be substituted with one or two substituents independently selected from the group consisting of, where Y is selected from O, S or Se, and R １０ C ６ ~C １２ Ariel, C ３ ~C １２ Heteroaryl, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, partially fluorinated, or perfluorinated C １ ~C ６ Alkyl, partially fluorinated, or perfluorinated C １ ~C ６ Alkoxy, partially deuterated, or hyperdeuterated C １ ~C ６ Alkyl, partially deuterated, or hyperdeuterated C １ ~C ６ Selected independently of alkoxy; Here, C on Z ６ ~C １２ Each aryl substituent is C １ ~C ４ They may be substituted with alkyl or halogen; G is selected such that the dipole moment of compound G-phenyl is between 1D and 7D; The first electron transport layer and the second electron transport layer do not contain an electrolytic dopant. The first electron transport layer has a thickness of 1 to 10 nm. The compound of formula (II) is excluded if it is a compound of the following formula: 【Chemistry 1】 Organic light-emitting diode.

2. Ar １ This is independently selected from the group consisting of phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa), 【Chemistry 2】 During the ceremony, The asterisk symbol "*" indicates the bonding position where the base of formula (IIa) is attached to A; R １ ~R ５ H, C ６ ~C １２ Aryl and C ４ ~C １０ Independently selected from the group consisting of heteroaryls, The organic light-emitting diode according to claim 1.

3. A is selected from the group consisting of phenylene, naphthylene, biphenylene, and terphenylene, which may or may not be substituted. The organic light-emitting diode according to claim 1.

4. X is independently selected from the group consisting of triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil, each of which may or may not be substituted. The organic light-emitting diode according to claim 1.

5. Ar ２ These are independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diadinyl, 1,3-diadinyl, 1,4-diadinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenatrolinyl, and dinaphthofuranil, each of which may or may not be substituted. The organic light-emitting diode according to claim 1.

6. G is dialkylphosfinyl, diarylphosfinyl, alkylarylphosfinyl, nitrile, benzonitrile, nicotinonitrile, amidoyl, carbamidoyl and C ２ ~C １７ Selected from the group consisting of heteroaryls; Each of G is a dialkylphosfinyl, diarylphosfinyl, alkylarylphosfinyl, nitrile, benzonitrile, nicotinonitrile, amidoyl, carbamidoyl, or C ２ ~C １７ It may contain one or more substituents bonded to a heteroaryl molecule, wherein the one or more substituents are selected from the group consisting of phenyl, methyl, ethyl, and pyridyl. The organic light-emitting diode according to claim 1.

7. G is independently selected from the group consisting of dimethylphosphenyl, diphenylphosphenyl, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridinyl, 2,2'-bipyridinyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinyl, and (pyridin-2-yl)imidazo[1,5-a]pyridinyl. The organic light-emitting diode according to claim 1.

8. G is selected such that the compound G-phenyl is represented by one of the following structures. 【Transformation 3】 【change】 【change】 【change】 The organic light-emitting diode according to claim 1.

9. The compound of formula (II) is selected from B-1 to B-25. 【Chemistry 4】 【change】 【change】 The organic light-emitting diode according to claim 1.

10. The second electron transport layer further comprises compound (III), which comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, and optionally 9 or 10 aromatic or heteroaromatic rings. The organic light-emitting diode according to claim 1.

11. The compound (III) contains 1 to 5 heteroaromatic rings, The organic light-emitting diode according to claim 10.

12. If the compound (III) contains two or more heteroaromatic rings, the heteroaromatic rings are separated from each other by at least one aromatic ring that does not contain heteroatoms. The organic light-emitting diode according to claim 10.

13. The first electron transport laminate is disposed between the first light-emitting layer and the charge-generating layer. The organic light-emitting diode according to claim 1.

14. The first electron transport layer and the second electron transport layer are in direct contact with each other. The organic light-emitting diode according to claim 1.

15. The second electron transport layer is in direct contact with the charge generation layer. The organic light-emitting diode according to claim 1.

16. The charge generating layer comprises a metal, or an alkali metal, a metal salt, or an alkaline earth metal salt and / or a rare earth metal salt, or an organic alkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof. The organic light-emitting diode according to claim 1.

17. An apparatus comprising an organic light-emitting diode according to any one of claims 1 to 16, The aforementioned device is a display device or a light-emitting device, and the light is emitted through a transparent cathode. Device.

18. An apparatus comprising an organic light-emitting diode according to any one of claims 1 to 16, The device is a display device or a light-emitting device, and the light is emitted through a transparent anode. Device.

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