Organic light-emitting diode and device including same

Abstract

The present invention relates to an organic light emitting diode comprising an opaque substrate, an anode, a cathode, a first light emitting layer, a second light emitting layer, a first charge generating layer and an 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 organic light emitting diodes and devices including same.

[0002] Organic light-emitting diodes (OLEDs), which are self-emissive devices, have wide viewing angles, excellent contrast, rapid response, high brightness, excellent driving voltage characteristics, and color reproducibility. A typical OLED includes an anode, a hole-transporting layer (HTL), an emissive layer (EML), an electron-transporting 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 and / or organometallic compounds.

[0003] When voltage is applied to the anode and cathode, holes injected from the anode electrode migrate to the EML through the HTL, and electrons injected from the cathode electrode migrate to the EML through the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons fall from the excited state to the ground state, light is emitted. The injection and flow of holes and electrons must be balanced, resulting in OLEDs with the above structure having excellent efficiency.

[0004] A variety of organic electronic diodes containing different electron transport materials are known in the art. However, there remains a need to improve the performance of such devices, particularly the performance of single-emissive-layer top-emitting OLEDs, particularly in terms of efficiency and voltage.

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

[0006] [Disclosure] The object is to provide a light-emitting device comprising an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack, the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is C6~C 60 Aryl or C2-C 42 heteroaryl; where Ar 1 Each is 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 1 C6~C above 12 aryl substituents, respectively, and Ar 1 C3~C above 11Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; A is C6~C 30 aryl; Here, each 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 )2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; X is C2~C 42 Heteroaryl and C6-C 60 aryl; Here, each X is C6 to C 12 Aryl, C3-C 11Heteroaryl 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Aryl substituents, respectively, and C3 to C on X 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; The molecular dipole moment of the compound of formula (I) is 0D or more and 4D or less; the second electron transport layer comprises a 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 is C2~C 42 Heteroaryl and C6-C 60 aryl; where Ar 2 Each is C6~C 12 Aryl, C3-C 11Heteroaryl 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 2 C6~C above 12 aryl substituents, respectively, and Ar 2 C3~C above 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; Z is C6~C 30 aryl; Here, Z is C6 to 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10)2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; G is selected such that the dipole moment of compound G-phenyl is greater than or equal to 1D and less than or equal to 7D; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; This is achieved by organic light-emitting diodes.

[0007] The object is further achieved by a device comprising an organic light emitting diode of the present invention, said device being a display device or a light emitting device.

[0008] [First Electron Transport Layer] The first electron transport layer comprises a compound of formula (I) (Ar 1 -A c ) a -X b (I).

[0009] The first electron transport layer can consist of a compound of formula (I). Alternatively, the first electron transport layer can consist of a mixture of a compound of formula (I) and one or more additional compounds, provided that none of the additional compounds are electrical dopants. The first electron transport layer can include two or more compounds of formula (I). In particular, the first electron transport layer can consist of a mixture of a compound of formula (I) and an additional compound known in the art as an electron transport matrix compound. Exemplary additional electron transport matrix compounds that can be included are disclosed below.

[0010] In compounds of formula (I), the group "A" (if present, i.e., when c>1) is a group Ar 1 and X. The compound of formula (I) may have two or more groups (Ar 1 -A c ), the group may or may not independently include a spacer A.

[0011] In compounds of formula (I), a and b are independently 1 or 2. Alternatively, a and b may both be 1.

[0012] In the compounds of formula (I), c is independently 0 or 1.

[0013] Ar 1 is 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-C 36 Heteroaryl or C6-C 36 Aryl or C2-C 30 Heteroaryl or C6-C 30 Aryl or C2-C 24 heteroaryl.

[0014] Ar 1 are independently C6 to 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 It may also be aryl.

[0015] Ar 1 are independently C2 to C 42 Heteroaryl, optionally C2-C 40 Heteroaryl, optionally C2-C 36 Heteroaryl, optionally C2-C 30 Heteroaryl, and optionally C2-C 24 It may also be heteroaryl.

[0016] In one embodiment, Ar 1 is different from X.

[0017] Ar 1 may contain a system of two or more fused aromatic rings, preferably three or more fused aromatic rings.

[0018] Ar 1 must have at least one sp 3 It may contain -hybridized carbon atoms.

[0019] Ar 1 is a carbon-carbon sp bond that is not incorporated into an aromatic ring structure. 2 It may contain at least one alkene bond. 1 is unsubstituted C2~C 42 In embodiments independently selected from heteroaryl, the heteroatom is connected to Ar by a single bond. 1 is bonded to the molecular structure of

[0020] Ar 1may 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).

[0021] [ka]

[0022] During the ceremony, The asterisk symbol "*" represents the attachment point for attaching the group of formula (IIa) to A; R 1 ~R 5 H, C6~C 12 Aryl and C3-C 10 heteroaryl, or C4-C5 heteroaryl.

[0023] Ar 1 may be independently selected from the group consisting of phenyl, anthracenyl, fluorenyl or a group of formula (IIa).

[0024] [ka]

[0025] In the formula, R 1 ~R 5 is independently selected from H and phenyl.

[0026] Ar 1 may be a group of formula (IIa).

[0027] [ka]

[0028] R 1 ~R5 At least two of them are not H.

[0029] In the group of formula (IIa), R which is not H 1 ~R 5 At least two of the R may be ortho to each other. 1 ~R 5 At least one of may be in the ortho position relative to the * position. In this regard, two groups are in the ortho position relative to each other when they are each attached to adjacent carbon atoms of the benzene ring in formula (IIa).

[0030] Ar 1 can be independently selected from one of the following groups:

[0031] [ka]

[0032] where each asterisk symbol "*" represents a bond position for bonding to A.

[0033] Ar 1 When is substituted, each of the substituents may be independently selected from the group consisting of phenyl, naphthyl, biphenyl, pyridyl, picolinyl, lutidinyl, dibenzofuranyl, dibenzothiophen-yl, and benzothiophen-yl.

[0034] A is a substituted or unsubstituted C6-C 30 Aryl or C6-C 24 Aryl or C6-C 18 aryl.

[0035] A may be independently selected from the group consisting of phenylene, naphthylene, biphenylene, and terphenylene, each of which may be substituted or unsubstituted.

[0036] A can be independently selected from one of the following groups or combinations thereof:

[0037] [ka]

[0038] where Ar 1 and the bonding position for bonding to X can be freely selected, and preferably can be as follows:

[0039] [ka]

[0040] When A is substituted, each substituent on A can be independently selected from the group consisting of phenyl and C1-C4 alkyl.

[0041] X is C2~C 39 Heteroaryl and C6-C 54 Aryl, optionally 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 aryl, each of which may be substituted or unsubstituted.

[0042] X is C2~C 39 N-containing heteroaryl, C2-C 39 O-containing heteroaryl and C6-C 54 Aryl, optionally C2-C 36 N-containing heteroaryl, C2-C36 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 aryl.

[0043] X is C2~C 39 N-containing heteroaryls and C-C 54 Aryl, optionally C2-C 36 N-containing heteroaryls and C-C 48 Aryl, optionally C3-C 30 N-containing heteroaryls and C-C 42 Aryl, optionally C3-C 27 N-containing heteroaryls and C-C 36 Aryl, optionally C3-C 24 N-containing heteroaryls and C-C 30 Aryl, and optionally C3-C 21 N-containing heteroaryls and C-C 24 aryl. In this regard, each N-containing heteroaryl may be defined as containing one or more N atoms as the only heteroatom.

[0044] X can be independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl, each of which can be substituted or unsubstituted.

[0045] X can be independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl, each of which can be substituted or unsubstituted.

[0046] X can be independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, and fluoranthenyl, each of which may be substituted or unsubstituted.

[0047] X can be independently selected from one of the following groups:

[0048] [ka]

[0049] In the formula, the asterisk symbol "*" represents the attachment point where each group is attached to A.

[0050] When X is substituted, each substituent on X may be independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl. When X is substituted, each substituent on X may be independently selected from the group consisting of phenyl and biphenyl-yl.

[0051] When X is substituted, each substituted X group is

[0052] [ka]

[0053] wherein the asterisk symbol "*" represents the respective attachment position for attaching a group to A.

[0054] Compounds of formula (I) may be defined as not containing the moiety P=O. Compounds of formula (I) may be defined as not containing P(=O)Aryl2. Compounds of formula (I) may be defined as not containing P(=O)Alkyl2. Compounds of formula (I) may be defined as not containing P(=O)Ph2. Compounds of formula (I) may be defined as not containing P(=O)(CH3)2. Compounds of formula (I) may be defined as not containing R'P(=O)R'' (where R' and R'' are joined together to form a ring), i.e., not containing a ring-phosphine oxide. Compounds of formula (I) may be defined as not containing R'P(=O)R'' (where R' and R'' are joined together to form a seven-membered ring).

[0055] A compound of formula (I) may be defined as not containing two moieties P=O. A compound of formula (I) may be defined as not containing two P(=O)Aryl2. A compound of formula (I) may be defined as not containing two P(=O)Alkyl2. A compound of formula (I) may be defined as not containing two P(=O)Ph2. A compound of formula (I) may be defined as not containing two P(=O)(CH3)2. A compound of formula (I) may be defined as not containing CN.

[0056] One or more of the following formulae may be defined as excluded from the scope of compounds of formula (I):

[0057] [ka]

[0058] 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, and optionally 9 to 11 aromatic or heteroaromatic rings. In this regard, the aromatic and heteroaromatic rings, respectively, are single aromatic rings, such as 6-membered aromatic rings (e.g., phenyl), 6-membered heteroaromatic rings (e.g., pyridyl), 5-membered heteroaromatic rings (e.g., pyrrolyl), etc. In fused (hetero)aromatic ring systems, each ring is considered a single ring in this regard. For example, naphthalene contains two aromatic rings.

[0059] Hybrid functional B3LYP and Gaussian 6-31G for compounds of formula (I) * Using the basis set, the molecular dipole moment calculated by the TURBOMOLE V6.5 program package can be greater than or equal to 0D and less than or equal to 4D; alternatively, greater than or equal to 0D and less than or equal to 3.5D; alternatively, greater than or equal to 0D and less than or equal to 3.0D; alternatively, greater than or equal to 0D and less than or equal to 2.5D; or alternatively, greater than or equal to 0D and less than or equal to 2.0D. In this regard, the dipole moment of a molecule containing an N atom

[0060]

number

[0061] is given by the following formula:

[0062]

number

[0063] During the ceremony,

[0064]

number

[0065] are the partial charges 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 determined by 6-31G in the gas phase, as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * The basis set is optimized using hybrid functional B3LYP. If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule.

[0066] In one embodiment, the hybrid function B3LYP and Gaussian 6-31G * The LUMO energy level of the compound of formula (I) on an absolute scale, with the vacuum energy level at zero, calculated using the basis set 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.

[0067] The compound of formula (I) can be selected from compounds A-1 to A-29 in Table 1 below.

[0068] [Table 1] JPEG0007807404000014.jpg232169JPEG0007807404000015.jpg211169JPEG00078074040 00016.jpg243169JPEG0007807404000017.jpg232169JPEG0007807404000018.jpg152169

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

[0070] The first electron transport layer may be disposed between the light-emitting layer and the second electron transport layer. The first electron transport layer may be disposed in direct contact with the light-emitting layer. The first electron transport layer may be disposed so as to be "sandwiched in contact" between the light-emitting layer and the second electron transport layer.

[0071] The first electron transport layer can have a thickness of less than 50 nm, optionally from 1 to 30 nm, optionally from 1 to 10 nm, optionally from 1 to 5 nm.

[0072] [Second Electron Transport Layer] The second electron transport layer comprises a compound of formula (II) (Ar 2 ) m -(Z k -G) n (II).

[0073] 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 a compound of formula (II) and one or more additional compounds, provided that none of the additional compounds are electrical dopants. The first electron transport layer may include two or more compounds of formula (II). The second electron transport layer may consist of a mixture of a compound of formula (II) and additional compounds known in the art as electron transport matrix compounds. Exemplary additional electron transport matrix compounds that may be included are disclosed below.

[0074] In compounds of formula (II), the group "Z" (if present, i.e., when k>1) is a group Ar 2 and G. The compound of formula (II) may have two or more groups (Z k-G), the group may or may not independently include a spacer Z.

[0075] In formula (II), m and n are independently 1 or 2. In formula (II), m and n may be 1.

[0076] In formula (II), k is independently 0, 1, or 2. In formula (II), k may be independently 1 or 2.

[0077] Ar 2 is C2~C 39 Heteroaryl and C6-C 54 Aryl, optionally 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 aryl.

[0078] Ar 2 is C2~C 39 N-containing heteroaryls and C-C 54 Aryl, optionally C2-C 36 N-containing heteroaryls and C-C 48 Aryl, optionally C3-C 30 N-containing heteroaryls and C-C 42 Aryl, optionally C3-C 27 N-containing heteroaryls and C-C 36 Aryl, optionally C3-C 24 N-containing heteroaryls and C-C 30 Aryl, and optionally C3-C 21 N-containing heteroaryls and C-C 24aryl. In this regard, each N-containing heteroaryl may be defined as containing one or more N atoms as the only heteroatom.

[0079] Ar 2 may contain at least two fused five- or six-membered rings.

[0080] Ar 2 may be independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl, each of which may be substituted or unsubstituted.

[0081] Ar 2 can be independently selected from the group consisting of dibenzoacridinyl, 1,3-diazinyl, 1,4-diazinyl, anthracenyl, triazinyl, phenanthrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranyl.

[0082] Ar 2 can be independently selected from one of the following groups:

[0083] [ka]

[0084] Here, the asterisk symbol "*" represents the bonding position for bonding to Z.

[0085] Ar 2 When is substituted, 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 be substituted or unsubstituted.

[0086] Ar 2 When is substituted, Ar 2 Each of the above substituents may be independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl.

[0087] Z is independent, C6~C 24 Aryl or C6-C 18 Aryl or C6-C 12 aryl, which may be substituted or unsubstituted.

[0088] Z may be selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene, each of which may be substituted or unsubstituted.

[0089] Z may be independently selected from one of the following groups:

[0090] [ka]

[0091] where Ar 2 The binding position to G can be freely selected.

[0092] When Z is substituted, each substituent on Z may be independently selected from the group consisting of phenyl and C1-C4 alkyl.

[0093] G is the hybrid function B3LYP and Gaussian 6-31G *The dipole moment of the compound G-phenyl, calculated using the TURBOMOLE V6.5 program package using the basis set, is selected to be 1D or more and 7D or less. The unit of dipole moment, "Debye", is abbreviated by the symbol "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 range or the following range. It has further been found that it is even more advantageous for the compound of formula (II) to contain an additional polar group (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 low (for example, if the compound is a symmetric molecule containing the same first polar group and second polar group, the dipole moment can 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 non-polar group "phenyl" are referred to instead. In this regard, the dipole moment of compounds containing N atoms

[0094]

number

[0095] is given by the following formula:

[0096]

number

[0097] During the ceremony,

[0098]

number

[0099] are the partial charges 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 determined by 6-31G in the gas phase, as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * The basis set is optimized using the hybrid functional B3LYP. If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule. In this regard, the entire moiety G encompasses all possible substituents that may be included.

[0100] G can be selected so 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 so that the dipole moment of compound G-phenyl is 7D or less, optionally 6.5D or less, optionally 6D or less, optionally 5.5D or less, or optionally 5D or less. When 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 to be within this range. Conformational isomerism is a form of stereoisomerism, and isomers can be interconverted simply by formal rotation about a single bond.

[0101] Selecting G such that the dipole moment of the compound G-phenyl is within the above ranges provides improved electron injection from an adjacent separate electron-injecting layer (EIL), reducing the voltage of the OLED device and increasing the cd / A efficiency of the OLED device.

[0102] Exemplary compounds "G-phenyl" are listed below in Table 2, where the moiety of each compound is

[0103] [ka]

[0104] specifies the "phenyl" portion of "G-phenyl."

[0105] [Table 2] JPEG0007807404000026.jpg249169JPEG0007807404000027.jpg229169JPEG000 7807404000028.jpg255169JPEG0007807404000029.jpg240169JPEG0007807404 000030.jpg244169JPEG0007807404000031.jpg255169JPEG0007807404000032. jpg228169JPEG0007807404000033.jpg253169JPEG0007807404000034.jpg98169

[0106] G is selected from the group consisting of dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, diheteroarylphosphinyl, arylheteroarylphosphinyl, cyclic diarylphosphinyl, phosphine oxide, aryl-containing phosphine oxide, heteroaryl-containing phosphine oxide, cyclic arylheteroarylphosphinyl, cyclic heteroaryl-containing phosphine oxide, nitrile, benzonitrile, nicotinonitrile, amide, carbamide, and C2-C 42 G may be selected from the group consisting of heteroaryl; G may include one or more substituents attached to the group, wherein one or more of the substituents is C-C 18 Aryl, C1-C 10 Alkyl, C2-C 14 Heteroaryl is selected from the group consisting of: In this regard, "cyclic" means that the "P=O" of phosphinyl, phosphine oxide, respectively, is part of a ring formed with the further moiety of the group.

[0107] G is di-C1~C 10 Alkylphosphinyl, di-C6-C10 Arylphosphinyl, C 10 ~C 42 Diheteroarylphosphinyl, C7-C 42 Arylheteroarylphosphinyl, C8-C 42 Phosphine oxides, C8-C 42 Aryl-containing phosphine oxides, C8-C 63 Heteroaryl-containing phosphine oxides, C 12 ~C 63 Cyclic arylphosphinyl, C7-C 42 Cyclic arylheteroarylphosphinyl, C7-C 42 Cyclic heteroaryl-containing phosphine oxides, and C2-C 39 Heteroaryl, optionally C2-C 35 Heteroaryl, optionally C2-C 32 Heteroaryl, optionally C2-C 29 Heteroaryl, optionally C2-C 25 G may be selected from the group consisting of heteroaryl; G may include one or more substituents attached to the group, wherein one or more of the substituents is C-C 12 Aryl, C1-C6 alkyl, C2-C 11 heteroaryl.

[0108] G is di-C1-C4 alkylphosphinyl, di-C6-C 10 Arylphosphinyl, C 10 Diheteroarylphosphinyl, C7-C 25 Arylheteroarylphosphinyl, C8-C 42 Phosphine oxides, C8-C 42 Aryl-containing phosphine oxides, C8-C 24 Heteroaryl-containing phosphine oxides, C 12 ~C 42 Cyclic arylphosphinyl, C7-C 25 Cyclic arylheteroarylphosphinyl, C7-C 25 Cyclic heteroaryl-containing phosphine oxides, and C2-C 25heteroaryl; each G may include one or more substituents attached to a group, wherein one or more of the substituents is selected from the group consisting of C-C 10 It is selected from the group consisting of aryl, C1-C4 alkyl, and C2-C5 heteroaryl.

[0109] G is dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, diheteroarylphosphinyl, arylheteroarylphosphinyl, cyclic diarylphosphinyl, phosphine oxide, aryl-containing phosphin oxide, heteroaryl-containing phosphin oxide, cyclic arylheteroarylphosphinyl, cyclic heteroaryl-containing phosphin oxide, nitrile, benzonitrile, nicotinonitrile, amido-yl, carbamido-yl, and C-C 17 and heteroaryl; each G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of phenyl, methyl, ethyl, and pyridyl.

[0110] G is dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, di-hydro-benzimidazolon-yl, diphenyl-propan-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, phenylbenzoquinolinyl, phenylbenzimidazoquinolinyl, pyridinyl, bipyridinyl, picolinyl, rutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl, quinazolinyl, benzoxazolyl, benzimidazolyl, pyridinyl-imidazopyridinyl;

[0111] [ka] JPEG0007807404000036.jpg213169JPEG0007807404000037.jpg163169JPEG0007807404000038.jpg207169

[0112] wherein the asterisk symbol "*" represents the point of attachment.

[0113] G represents 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;

[0114] [ka] JPEG0007807404000040.jpg213169JPEG0007807404000041.jpg215169JPEG0007807404000042.jpg202169JPEG0007807404000043.jpg87169

[0115] wherein the asterisk symbol "*" represents the point of attachment.

[0116] The compound of formula (II) can be selected from compounds B-1 to B-26 in Table 3 below.

[0117] [Table 3] JPEG0007807404000045.jpg233169JPEG0007807404000046.jpg254169JPEG0007807404000047.jpg254169JPEG0007807404000048.jpg238169

[0118] In one embodiment, the hybrid function B3LYP and Gaussian 6-31G * The LUMO energy level of the compound of formula (II) in the absolute scale, with the vacuum energy level at zero, calculated using the basis set by the TURBOMOLE V6.5 program package is in the range of −2.30 eV to −1.20 eV, preferably −2.10 eV to −1.28 eV.

[0119] In one embodiment, the compound of formula (II) contains one polar group "G".

[0120] Compounds of formula (II) may be defined as not containing the moiety P=O. Compounds of formula (II) may be defined as not containing P(=O)Aryl2. Compounds of formula (II) may be defined as not containing P(=O)Alkyl2. Compounds of formula (II) may be defined as not containing P(=O)Ph2. Compounds of formula (II) may be defined as not containing P(=O)(CH3)2. Compounds of formula (II) may be defined as not containing R'P(=O)R'' (where R' and R'' are joined together to form a ring), i.e., not containing a ring-phosphine oxide. Compounds of formula (II) may be defined as not containing R'P(=O)R'' (where R' and R'' are joined together to form a seven-membered ring).

[0121] A compound of formula (II) may be defined as not containing two moieties P=O. A compound of formula (II) may be defined as not containing two P(=O)Aryl2. A compound of formula (II) may be defined as not containing two P(=O)Alkyl2. A compound of formula (II) may be defined as not containing two P(=O)Ph2. A compound of formula (II) may be defined as not containing two P(=O)(CH3)2. A compound of formula (II) may be defined as not containing CN.

[0122] One or more of the following formulas may be defined as excluded from the scope of compounds of formula (II):

[0123] [ka]

[0124] When the second electron transport layer comprises a compound of formula (II) and a compound (III), the following combinations of compounds in the specified amounts (see Tables 3 and 4) may be specified to be excluded:

[0125] B-24:C-3 30:70 v:v; C-3:B-11 30:70 v:v; B-24:C-5 30:70 v:v; B-11:C-5 30:70 v:v; B-24:C-6 30:70 v:v; B-11:C-6 30:70 v:v.

[0126] The following compounds

[0127] [ka]

[0128] The following organic light emitting diodes a) and b) may be excluded, including: a) The electron transport layer is formed of Compound E

[0129] [ka]

[0130] and disposed adjacent to and in direct contact with an n-doped charge generating layer made of metallic lithium (the weight ratio of E:Li is equal to 98:2), wherein the composition of the electron transport layer is selected from B-24:C-3, B-10:C-3, B-24:C-5, B-11:C-5, B-24:C-6, B-11:C-6, and the weight ratio of the first and second components in each of these compositions is 30:70; b) A top-emitting blue OLED having the following structure:

[0131] [Table 4]

[0132] (In the table, HT-3 is

[0133] [ka]

[0134] and F2 is

[0135] [ka]

[0136] and C-1 is

[0137] [ka]

[0138] and D-1 is

[0139] [ka]

[0140] , H09 is a commercially available blue-emitting host, and BD200 is a commercially available blue emitter, both supplied by SFC, Korea).

[0141] The second electron transport layer may further comprise a compound (III), wherein 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, wherein one or more aromatic or heteroaromatic rings may be substituted with C1-C4 alkyl. In this regard, the aromatic ring, respectively the heteroaromatic ring, is a single aromatic ring, for example, a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl, etc. In a fused (hetero)aromatic ring system, each ring is considered a single ring in this regard. For example, naphthalene contains two aromatic rings.

[0142] Compound (III) may contain at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.

[0143] The aromatic or heteroaromatic ring of compound (III) may be a six-membered ring.

[0144] The heteroaromatic rings of compound (III) may be N-containing heteroaromatic rings, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, and optionally all of the heteroaromatic rings contain N as the only type of heteroatom.

[0145] Compound (III) can comprise at least one 6-membered heteroaromatic ring containing 1 to 3 N atoms in each heteroaromatic ring, and optionally 1 to 3 6-membered heteroaromatic rings each containing 1 to 3 N atoms in each heteroaromatic ring.

[0146] At least one six-membered heteroaromatic ring contained in compound (III) may be an azine, a triazine, a diazine, or a pyrazine.

[0147] When compound (III) contains two or more heteroaromatic rings, the heteroaromatic rings may be separated from one another by at least one aromatic ring that does not contain a heteroatom.

[0148] In one embodiment, the heteroatom in the heteroaromatic ring of compound (III) is attached to the molecular structure of compound (III) by at least one double bond.

[0149] Hybrid functional B3LYP and Gaussian 6-31G for compound (III) * Using the basis set, the molecular dipole moment calculated by the TURBOMOLE V6.5 program package can be greater than or equal to 0D and less than or equal to 4D; alternatively, greater than or equal to 0.1D and less than or equal to 3.9D; alternatively, greater than or equal to 0.2D and less than or equal to 3.7D; or alternatively, greater than or equal to 0.3D and less than or equal to 3.5D.

[0150] The selection of compound (III) according to these embodiments provides further improvement in the mobility of the second electron transport layer, reducing the voltage of the OLED device and increasing the cd / A efficiency of the OLED device.

[0151] In one embodiment, compound (III) is not a compound of formula (II). The compound of formula (III) can be selected from compounds C-1 to C-6 in Table 4 below.

[0152] [Table 5] JPEG0007807404000058.jpg103169

[0153] When the second electron transport layer comprises both the compound of Formula (II) and compound (III), the weight ratio of Formula (II) to compound (III) may be 1:99 to 99:1, alternatively 10:90 to 60:40, alternatively 20:80 to 50:50, alternatively 25:75 to 40:60, or alternatively about 30:70.

[0154] In one embodiment, the hybrid function B3LYP and Gaussian 6-31G * The LUMO energy level of the compound of formula (III) in the absolute scale, with the vacuum energy level at zero, calculated by the TURBOMOLE V6.5 program package using the basis set is in the range of −2.00 eV to −1.70 eV, preferably −1.95 eV to −1.80 eV.

[0155] In one embodiment, compound (III) contains one nitrogen-containing six-membered ring.

[0156] In another embodiment, compound (III) contains two nitrogen-containing six-membered rings.

[0157] In one embodiment, the compound of formula (I) is not a compound of formula (II). In a further embodiment, the compound of formula (II) is not compound (III). In another embodiment, the compound of formula (I) is not compound (III). In a further embodiment of the present invention, all three compounds, i.e., the compound of formula (I), the compound of formula (II) and compound (III), differ from each other in that they have different molecular structural formulas.

[0158] The second electron transport layer may be disposed between the first electron transport layer and the electron injection layer, the second electron transport layer may be disposed in direct contact with the first electron transport layer, or the second electron transport layer may be disposed "sandwiched in contact" with the first electron transport layer and the electron injection layer.

[0159] The second electron transport layer can have a thickness of less than 100 nm, optionally from 10 to 90 nm, optionally from 10 to 60 nm, optionally from 10 to 50 nm.

[0160] [Additional Possible Properties of OLEDs] In the context of the present disclosure, a stack is an arrangement of two or more distinct layers. The layers of the stack may be distinguished from one another by the chemical nature of the materials contained in each layer, i.e., they may be made of different compounds. An electron transport stack in the context of the present disclosure includes at least two distinct layers, each made of an electron transport material.

[0161] The compounds of formula (I) and (II) may be different from each other, i.e., the compounds of formula (I) and (II) may differ from each other in at least one structural aspect, in particular at least one atom and / or group.

[0162] The first electron transport layer and the second electron transport layer do not contain an electrical dopant. In this regard, "does not contain" means that the respective layers contain only the respective compounds (electrical dopants) that cannot be avoided by ordinary purification methods and common technical means during the preparation of the respective layers. In this regard, the electrical dopant is particularly, but not limited to, an electrical n-dopant. The electrical n-dopant may be selected from metals, alkali metals, metal salts, alkaline earth metal salts and / or rare earth metal salts, organic alkali metal complexes, alkali metal complexes, LiF, LiCl, LiBr, LiI, LiQ, metal borates, or mixtures thereof. In particular, the first electron transport layer and the second electron transport layer may not contain an electrical n-dopant. The electrical n-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 borate salts.

[0163] In this regard, the electrical n-dopant is particularly, but not limited to, an elemental metal or an electropositive 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 can be LiF, LiCl, LiBr, LiI, metal borates, metal quinolinolates, or mixtures thereof. Another example of an electrical n-dopant is a strong chemical reducing agent. This type of "reductive" n-dopant can generally be characterized by a highest occupied molecular orbital (HOMO) energy level that is comparable to the lowest unoccupied molecular orbital energy level of the corresponding electron-transporting matrix, which is approximately -3.0 eV or less for typical OLED transport materials. The term "about -3.0 eV or less" should be understood to mean values ​​less negative than -3.0 eV, for example, -2.8 eV, -2.5 eV, -2.3 eV, -2.1 eV, or values ​​less negative than -2.0 eV.

[0164] The electrical n-dopant may be an organic compound such as those disclosed in EP1837926A1, WO07107306A1 or WO07107356A1.

[0165] An electrical dopant is defined as one that is non-emissive in nature.

[0166] The first electron transport layer and the second electron transport layer may be in direct contact with each other.

[0167] The electron transport stack may consist of a first electron transport layer and a second electron transport layer.

[0168] The second electron transport layer may be in direct contact with the electron injection layer.

[0169] The electron injection layer may consist of several individual electron injection sublayers.

[0170] The electron injection layer may comprise a metal, or an alkali metal, 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.

[0171] The electron injection layer may consist of a metal, or an alkali metal, 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.

[0172] The compound of formula (II) may be specified as not being included in the electron injection layer. The compound of formula (I) may be specified as not being included in the electron injection layer. The compound of formula (III) may be specified as not being included in the electron injection layer.

[0173] The compound of formula (I), the compound of formula (II) and the compound (III) may be different from each other and / or may not be contained in the electron injection layer.

[0174] Exemplary Embodiments According to one embodiment, the device comprises an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is C6~C 30 Aryl or C2-C 24heteroaryl; where Ar 1 Each is 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 1 C6~C above 12 aryl substituents, respectively, and Ar 1 C3~C above 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; A is C6~C 18 aryl; Here, each 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 )2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; X is C3~C 21 Heteroaryl and C6-C 24 aryl; Here, each X is C6 to 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, wherein Y is selected from O, S, or Se, preferably O, and R10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Aryl substituents, respectively, and C3 to C on X 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; The molecular dipole moment of the compound of formula (I) is 0 D or more and 3.5 D or less; the second electron transport layer comprises a 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 is C3~C 30 Heteroaryl and C6-C 42 aryl; where Ar 2 Each is 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, wherein Y is selected from O, S, or Se, preferably O, and R10 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 2 C6~C above 12 aryl substituents, respectively, and Ar 2 C3~C above 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; Z is C6~C 18 aryl; Here, Z is C6 to 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 )2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; G is selected such that the dipole moment of compound G-phenyl is greater than or equal to 2D and less than or equal to 6D; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0175] According to one embodiment, the device comprises an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is C6~C 30 aryl; where Ar 1 each optionally 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 aryl; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is C3~C 21 N-containing heteroaryl, C3-C 21 O-containing heteroaryl and C6-C 24 aryl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The compound of formula (I) has a molecular dipole moment of 0 D or more and 3.0 D or less; the second electron transport layer comprises a 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 is C3~C 21 Heteroaryl and C6-C 24 aryl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is C6~C 18 aryl; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, nitrile, benzonitrile, nicotinonitrile, amide, carbamide, and C2-C 42 heteroaryl; G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C-C 18 Aryl, C1-C 10 Alkyl, C2-C 14 selected from the group consisting of heteroaryl; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0176] According to one embodiment, the device comprises an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 are independently selected from phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl or a group having formula (IIa),

[0177] [ka]

[0178] During the ceremony, The asterisk symbol "*" represents the attachment point for attaching the group of formula (IIa) to A; R 1 ~R 5 H, C6~C 12 Aryl and C3-C 10 or C4-C5 heteroaryl, Here, each Ar 1 is optionally 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 independently selected from phenylene, naphthylene, biphenylene, and terphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is C3~C 21N-containing heteroaryls and C-C 24 aryl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The compound of formula (I) has a molecular dipole moment of 0 D or more and 2.5 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 is C3~C 21 N-containing heteroaryls and C-C 24 aryl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is C2 to C 25 heteroaryl; G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C-C 12 Aryl, C1-C6 alkyl, C2-C 11 selected from the group consisting of heteroaryl; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0179] According to one embodiment, the device comprises an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is independently selected from the group consisting of phenyl, anthracenyl, fluorenyl or a group of formula (IIa),

[0180] [ka]

[0181] In the formula, R 1 ~R 5 is independently selected from H and phenyl; where Ar 1 each optionally 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 independently selected from phenylene, naphthylene, biphenylene, and terphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The compound of formula (I) has a molecular dipole moment of 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is di-C1-C4 alkylphosphinyl, di-C6-C 10Arylphosphinyl, and C2-C 25 heteroaryl; wherein each G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C6-C 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 an electrical dopant; An organic light emitting diode is provided.

[0182] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is a group of formula (IIa),

[0183] [ka]

[0184] R 1 ~R 5 At least two of them are not H; where Ar 1 each optionally 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 independently selected from phenylene and biphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of dibenzoacridinyl, 1,3-diazinyl, 1,4-diazinyl, anthracenyl, triazinyl, phenanthrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranyl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, di-hydro-benzimidazolon-yl, diphenyl-propan-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl phenylbenzoquinolinyl, phenylbenzimidazoquinolinyl, pyridinyl, bipyridinyl, picolinyl, rutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl and pyridinyl-imidazopyridinyl; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0185] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is a group of formula (IIa),

[0186] [ka]

[0187] R 1 ~R 5 At least two of the R are not H, where R is not H. 1 ~R 5At least two of the R are ortho to each other and / or are not H. 1 ~R 5 At least one of * in the ortho position relative to the position of In the formula, Ar 1 each optionally 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 independently selected from phenylene and biphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, and fluoranthenyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of dibenzoacridinyl, 1,3-diazinyl, 1,4-diazinyl, anthracenyl, triazinyl, phenanthrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranyl; where Ar 2each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; 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 an electrical dopant; An organic light emitting diode is provided.

[0188] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack 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-26 shown in Table 3; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0189] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 are independent, C6~C 30 Aryl or C2-C 24 heteroaryl; where Ar 1 Each is 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 1 C6~C above 12 aryl substituents, respectively, and Ar 1 C3~C above 11Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; A is C6~C 18 aryl; Here, each 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10 )2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on A 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; X is C3~C 21 Heteroaryl and C6-C 24 aryl; Here, each X is C6 to C 12 Aryl, C3-C 11Heteroaryl 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on X 12 Aryl substituents, respectively, and C3 to C on X 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; The molecular dipole moment of the compound of formula (I) is 0 D or more and 3.5 D or less; the second electron transport layer comprises a 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 is C3~C 30 Heteroaryl and C6-C 42 aryl; where Ar 2 Each is C6~C 12 Aryl, C3-C 11Heteroaryl 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, wherein Y is selected from O, S, or Se, preferably O, and R 10 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; where Ar 2 C6~C above 12 aryl substituents, respectively, and Ar 2 C3~C above 11 Each heteroaryl substituent may be optionally substituted with C1-C4 alkyl or halogen; Z is C6~C 18 aryl; Here, Z is C6 to 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy, halogen, CN or PY(R 10)2, wherein Y is selected from O, S, or Se, preferably O, and R 10 is 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 perdeuterated C1-C6 alkyl, partially deuterated or perdeuterated C1-C6 alkoxy; Here, C6~C on Z 12 Each aryl substituent may be optionally substituted with C1-C4 alkyl or halogen; G is selected such that the dipole moment of compound G-phenyl is greater than or equal to 2D and less than or equal to 6D; The second electron transport layer may further comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0190] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is C6~C 30 aryl; where Ar 1each optionally 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 aryl; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is C3~C 21 N-containing heteroaryl, C3-C 21 O-containing heteroaryl and C6-C 24 aryl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The compound of formula (I) has a molecular dipole moment of 0 D or more and 3.0 D or less; the second electron transport layer comprises a 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 is C3~C 21 Heteroaryl and C6-C 24 aryl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is C6~C 18 aryl; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, nitrile, benzonitrile, nicotinonitrile, amide, carbamide, and C2-C 42 heteroaryl; wherein G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C-C 18 Aryl, C1-C 10 Alkyl, C2-C 14 selected from the group consisting of heteroaryl; The second electron transport layer may further comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) contains at least one heteroaromatic ring; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0191] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 are independently selected from phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa):

[0192] [ka]

[0193] During the ceremony, The asterisk symbol "*" represents the attachment point for attaching the group of formula (IIa) to A; R 1 ~R 5 H, C6~C 12 Aryl and C3-C 10 or C4-C5 heteroaryl, Here, each Ar 1 is optionally 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 independently selected from phenylene, naphthylene, biphenylene, and terphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is C3~C 21 N-containing heteroaryls and C-C 24 aryl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.5 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 is C3~C 21 N-containing heteroaryls and C-C 24aryl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is C2 to C 25 heteroaryl; G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C-C 12 Aryl, C1-C6 alkyl, C2-C 11 selected from the group consisting of heteroaryl; The second electron transport layer may further comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) contains 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 an electrical dopant; An organic light emitting diode is provided.

[0194] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is independently selected from the group consisting of phenyl, anthracenyl, fluorenyl or a group of formula (IIa),

[0195] [ka]

[0196] In the formula, R 1 ~R 5 is independently selected from H and phenyl; where Ar 1 each optionally 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 independently selected from phenylene, naphthylene, biphenylene, and terphenylene; Each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is di-C1-C4 alkylphosphinyl, di-C6-C 10 Arylphosphinyl, and C2-C 25 heteroaryl; each G may include one or more substituents attached to the group, wherein one or more of the substituents is selected from the group consisting of C-C 10 selected from the group consisting of aryl, C1-C4 alkyl, and C2-C5 heteroaryl; The second electron transport layer may further comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) contains 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 an N-containing heteroaromatic ring; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0197] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is a group of formula (IIa),

[0198] [ka]

[0199] R 1 ~R 5 At least two of them are not H; In the formula, Ar 1 each optionally 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 independently selected from phenylene and biphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of dibenzoacridinyl, 1,3-diazinyl, 1,4-diazinyl, anthracenyl, triazinyl, phenanthrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranyl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; G is selected from the group consisting of dimethylphosphinyl, diphenylphosphinyl, nitrile, benzonitrile, nicotinonitrile, di-hydro-benzimidazolon-yl, diphenyl-propan-yl, N,N-dimethylacetamide, amide, carbamide, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl phenylbenzoquinolinyl, phenylbenzimidazoquinolinyl, pyridinyl, bipyridinyl, picolinyl, rutidenyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinolinyl, phenanthrolinyl, phenylphenanthrolinyl and pyridinyl-imidazopyridinyl; The second electron transport layer may further comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) contains 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 an N-containing heteroaromatic ring; Compound (III) may contain at least one 6-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 an electrical dopant; An organic light emitting diode is provided.

[0200] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of Formula (I): (Ar 1 -A c ) a -X b (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar 1 is a group of formula (IIa),

[0201] [ka]

[0202] R 1 ~R 5 At least two of the R are not H, where R is not H. 1 ~R 5 At least two of the R are ortho to each other and / or are not H. 1 ~R 5 At least one of * in the ortho position relative to the position of In the formula, Ar 1 each optionally 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 independently selected from phenylene and biphenylene; wherein each A is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzacridinyl, dibenzoacridinyl, and fluoranthenyl; wherein each X is optionally substituted with one or two substituents independently selected from the group consisting of phenyl, naphthyl, and biphenyl-yl; The molecular dipole moment of the compound of formula (I) is 0 D or more and 2.0 D or less; the second electron transport layer comprises a compound of Formula (II): (Ar 2 ) m -(Z k -G) n (II); m and n are independently 1 or 2; k is independently 1 or 2; Ar 2 are independently selected from the group consisting of dibenzoacridinyl, 1,3-diazinyl, 1,4-diazinyl, anthracenyl, triazinyl, phenanthrolinyl, triphenylenyl, pyridinyl, and dinaphthofuranyl; where Ar 2 each optionally substituted with one or two substituents independently selected from the group consisting of phenyl, pyridinyl, and biphenyl-yl, optionally para-biphenyl-yl; Z is independently selected from the group consisting of phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene; wherein each Z is optionally substituted with one or two substituents independently selected from the group consisting of phenyl and C1-C4 alkyl; 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 comprise a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; Compound (III) contains 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 an N-containing heteroaromatic ring; Compound (III) may contain at least one 6-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 an electrical dopant; An organic light emitting diode is provided.

[0203] According to one embodiment, a light-emitting device includes an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack 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 1-1 to C-6 shown in Table 4; the first electron transport layer and the second electron transport layer do not contain an electrical dopant; An organic light emitting diode is provided.

[0204] [Further Layers] According to the present invention, the organic electronic device may include additional layers in addition to those described above, and exemplary embodiments of each layer are described below.

[0205] 〔substrate〕 The opaque substrate may be any respective substrate commonly used in the manufacture of electronic devices such as organic light emitting diodes, etc. Since light is emitted through the top surface, the substrate is an opaque material such as, for example, a plastic substrate, a metal substrate, a glass substrate coated with an opaque layer, for example an opaque anode layer, or a silicon substrate.

[0206] [Anode electrode] Either the first electrode or the second electrode included in the organic electronic device of the present invention may be an anode electrode. The anode electrode may be formed by evaporating or sputtering 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 (SnO), 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.

[0207] [Hole injection layer] The hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, etc. When the HIL is formed using vacuum deposition, the deposition conditions can be varied according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, in general, the conditions for vacuum deposition include a deposition temperature of 100°C to 500°C, a temperature of 10 -8 ~10 -3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm / sec.

[0208] When the HIL is formed using spin coating or printing, the coating conditions can be varied depending on the compound used to form the HIL and the desired structural and thermal properties of the HIL. For example, the coating conditions can 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 coating.

[0209] The HIL can be formed from any compound commonly used to form a HIL. Examples of compounds that can be used to form a 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).

[0210] The HIL can comprise or consist of a p-type dopant, which can be selected from, but is 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). The HIL can be selected from a hole-transporting matrix compound doped with a p-type dopant. Typical examples of known doped hole transport materials include copper phthalocyanine (CuPc) doped with tetrafluorotetracyanoquinone dimethane (F4TCNQ) having a LUMO level of approximately -5.2 eV, zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV), α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ, and α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalonnitrile. The p-type dopant concentration can be selected from 1% to 20% by weight, more preferably 3% to 10% by weight.

[0211] The thickness of the HIL can be in the range of about 1 nm to about 100 nm, and for example, about 1 nm to about 25 nm. If the thickness of the HIL is within this range, the HIL can have excellent hole injection properties without a substantial penalty in drive voltage.

[0212] [Hole transport layer] The hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for vacuum deposition or solution deposition can vary depending on the compound used to form the HTL.

[0213] The HTL can be formed from any compound commonly used to form an HTL. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which is incorporated by reference. Examples of compounds that can be used to form the HTL 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(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and suppress the diffusion of excitons into the EML.

[0214] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. A preferred thickness of the HTL may be 170 nm to 200 nm.

[0215] If the thickness of the HTL is within this range, the HTL can have excellent hole transport properties without a substantial penalty in driving voltage.

[0216] [Electron blocking layer] The function of the electron blocking layer (EBL) is to prevent electrons from migrating from the emissive layer to the hole transport layer, thereby confining the electrons to the emissive layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. The triarylamine compound 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.

[0217] If the electron blocking layer has a high triplet level, the electron blocking layer may also be described as a triplet control layer.

[0218] 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 light-emitting efficiency of the phosphorescent light-emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet level higher than that of the phosphorescent emitter in the adjacent light-emitting layer. Compounds suitable for triplet control layers, particularly triarylamine compounds, are described in EP 2 722 908 A1.

[0219] [Emitting layer (EML)] The EML can be formed on the HTL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the EML.

[0220] The light-emitting layer may be defined as being free of compounds of formula (I), formula (II) and / or compound (III).

[0221] The light-emitting layer (EML) may be formed by combining a host and an emitter dopant. Examples of hosts include Alq, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)).

[0222] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via the thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0223] Examples of red emitter dopants include, but are not limited to, PtOEP, Ir(piq)3, and Btp2lr(acac). These compounds are phosphorescent emitters, but fluorescent red emitter dopants can also be used.

[0224] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0225] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3, as well as ter-fluorene. 4,4'-Bis(4-diphenylamiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0226] The content of the emitter dopant can be about 0.01 to about 50 parts by weight per 100 parts by weight of the host. Alternatively, the light-emitting layer can 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 in driving voltage.

[0227] [Hole Blocking Layer (HBL)] A hole-blocking layer (HBL) can be formed on the EML to prevent hole diffusion into the ETL by vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, etc. If the EML contains a phosphorescent dopant, the HBL can also have a triplet exciton blocking function.

[0228] The HBL may also be named auxiliary ETL or a-ETL.

[0229] When the HBL is formed using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form HBL can be used. Examples of compounds for forming HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0230] The HBL can have a thickness of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole-blocking properties without a substantial penalty in driving voltage.

[0231] [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 the first electron transport layer and the second electron transport layer as defined herein. Furthermore, the OLED may comprise an additional ETL, which may or may not be as defined above. If the additional ETL is not as defined above, its properties may be as follows:

[0232] According to various embodiments, an OLED can include an electron transport stack including at least a first electron transport layer (ETL-1) comprising a compound of Formula (I) and at least a second electron transport layer (ETL-2) comprising a compound of Formula (II).

[0233] By properly adjusting the energy levels of specific layers of the ETL, electron injection and transport can be controlled, and holes can be efficiently blocked, resulting in OLEDs with long lifetimes, improved performance, and stability.

[0234] [Electron injection layer (EIL)] The EIL can facilitate electron injection from the cathode into the electron transport stack and can be formed on the electron transport stack, preferably directly on the electron transport stack, or preferably directly on a second electron transport layer, preferably in direct contact with the second electron transport layer. Examples of materials for forming or included in the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, LiO, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the materials used to form the EIL. The EIL may also 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.

[0235] The EIL can be composed of several individual EIL sublayers. When the EIL is composed of several individual EIL sublayers, the number of sublayers is preferably 2. The individual EIL sublayers can include various materials to form the EIL.

[0236] The thickness of the EIL can be in the range of about 0.1 nm to about 10 nm, for example, in the range of about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have good electron injection properties without a substantial penalty in driving voltage.

[0237] The electron transport stack of the present invention is not part of the electron injection layer.

[0238] [Cathode electrode] The cathode electrode is formed on the EIL, if present, preferably directly on the EIL, preferably in direct contact with the EIL. In the sense of the present invention, the cathode and EIL can be considered as a single functional part that allows electron injection into the electron transport stack. The cathode electrode may be formed from a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may 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.

[0239] The thickness of the cathode electrode may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode may be transparent or semi-transparent, even if it is formed from a metal or metal alloy. A transparent or semi-transparent cathode can facilitate light emission through the cathode.

[0240] It should be understood that the cathode electrode and the electron injection layer are not part of the electron transport stack.

[0241] [Organic Light-Emitting Diode (OLED)] The organic electronic device according to the present invention is an organic light-emitting device.

[0242] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an emissive layer, an electron transport stack, and a cathode electrode.

[0243] According to one aspect of the present invention, there is provided an organic light-emitting diode (OLED) comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, an electron transport stack, an electron injection layer, and a cathode electrode.

[0244] According to another aspect of the present invention, there is provided an OLED comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport stack, and a cathode electrode.

[0245] According to another aspect of the present invention, there is provided an OLED comprising: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport stack, an electron injection layer, and a cathode electrode.

[0246] According to various embodiments of the present invention, an OLED may be provided in which a layer is disposed between the layers described above, on the substrate, or on the top electrode.

[0247] According to one embodiment, an OLED can have a layered structure in which a substrate is disposed adjacent to an anode electrode, the anode electrode is disposed adjacent to a first hole injection layer, the first hole injection layer is disposed adjacent to a first hole transport layer, the first hole transport layer is disposed adjacent to a first electron blocking layer, the first electron blocking layer is disposed adjacent to a first light-emitting layer, the first light-emitting layer is disposed adjacent to a first electron transport layer, the first electron transport layer is disposed adjacent to a second electron transport layer, the second electron transport layer is disposed adjacent to the electron injection layer, and the electron injection layer is disposed adjacent to a cathode electrode.

[0248] For example, the OLED (100) according to FIG. 1 may be formed by a process in which an anode (120), a hole injection layer (130), a hole transport layer (140), an emissive layer (150), an electron transport stack (160) comprising a first electron transport layer (161) and a second electron transport layer (162), an electron injection layer (180), and a cathode electrode (190) are successively formed on a substrate (110) in this order.

[0249] For example, the OLED (100) according to Figure 2 may be formed by a process in which an anode (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), an emissive layer (150), an electron transport stack (160) comprising a first electron transport layer (161) and a second electron transport layer (162), an electron injection layer (180), and a cathode electrode (190) are successively formed on a substrate (110), in that order.

[0250] According to another aspect of the present invention, there is provided a method of manufacturing an organic electronic device, the method comprising: at least one evaporation source, preferably two evaporation sources, more preferably at least three evaporation sources.

[0251] Methods for deposition that may be suitable include: -Deposition by vacuum thermal evaporation; - deposition by solution processing (preferably, the processing is selected from spin-coating, printing, casting); and / or -Slot-die coating.

[0252] When the second electron transport layer comprises compound (III) and the compound of formula (II), the two compounds may be deposited by co-evaporation from two separate deposition sources, or may be deposited as a premix from a single deposition source. A premix is ​​a mixture of at least two compounds, which is prepared before being charged into the deposition source.

[0253] According to various embodiments of the present invention, the method may further include forming an emitting layer and at least one layer on the anode electrode, wherein forming the at least one layer is selected from the group consisting of forming a hole injection layer, forming a hole transport layer, or forming a hole blocking layer between the anode electrode and the first electron transport layer.

[0254] According to various embodiments of the present invention, the method may further include forming an organic light emitting diode (OLED), a first anode electrode formed on a substrate; a light-emitting layer formed on the first anode electrode; an electron transport stack formed on the light-emitting layer, and optionally a hole blocking layer formed on the light-emitting layer and an electron injection layer formed on the electron transport layer; -Finally, the cathode electrode is formed, optionally, a hole injection layer, a hole transport layer, and a hole blocking layer are formed in that order between the first anode electrode and the light-emitting layer; An electron injection layer is formed between the electron transport stack and the cathode electrode.

[0255] According to various embodiments of the present invention, the method further includes forming an electron injection layer on the organic semiconductor layer. According to various embodiments, the OLED can have the following layered structure, where the layers have the following order: an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, an emissive layer, an optional hole blocking layer, an electron transport stack, an electron injection layer, and a cathode.

[0256] According to another aspect of the present invention, there is provided an electronic device comprising at least one organic light emitting device according to any embodiment described throughout the present application, preferably the electronic device comprises an organic light emitting diode in one of the embodiments described throughout the present application, more preferably the electronic device is a display device.

[0257] In one embodiment, the organic electronic device according to the present invention may further comprise a layer comprising a radialene compound and / or a quinodimethane compound.

[0258] In one embodiment, the radialene compound and / or the quinodimethane compound may be substituted with one or more halogen atoms and / or one or more electron-withdrawing groups. The electron-withdrawing groups may be selected from a nitrile group, a halogenated alkyl group, a perhalogenated alkyl group, or a perfluorinated alkyl group. Other examples of the electron-withdrawing group may be an acyl group, a sulfonyl group, or a phosphoryl group.

[0259] Alternatively, the acyl group, sulfonyl group, and / or phosphoryl group may comprise halogenated and / or perhalogenated hydrocarbyl. In one embodiment, the perhalogenated hydrocarbyl may be perfluorinated hydrocarbyl. Examples of perfluorinated hydrocarbyl may be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, and perfluorotolyl; Examples of sulfonyl groups containing halogenated hydrocarbyl may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, etc.

[0260] In one embodiment, the radialene and / or quinodimethane compound may be included in a hole injection layer, a hole transport layer, and / or a hole generation layer.

[0261] In one embodiment, the radialene compound may have the formula (XX) and / or the quinodimethane compound may have the formula (XXIa) or (XXIb):

[0262] [ka]

[0263] (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 are independently selected from the electron-withdrawing groups listed above, and R 9 , R 10 , R 13 , R14 , R 17 , R 18 , R 19 , R 22 , R 23 and R 24 are independently selected from H, halogens, and electron-withdrawing groups as described above).

[0264] The following examples will be used to explain the present invention in more detail. However, the present invention is not limited to the following examples. Here, exemplary embodiments will be described in detail.

[0265] [General definition] Unless otherwise defined herein, "alkyl group" may refer to an aliphatic hydrocarbon group. An alkyl group may refer to a "saturated alkyl group" that does not have a double or triple bond. As used herein, the term "alkyl" is intended to include straight-chain, branched, and cyclic alkyls. For example, C3-alkyl may be selected from n-propyl and isopropyl. Similarly, C4-alkyl includes n-butyl, sec-butyl, and t-butyl. Similarly, C6-alkyl includes n-hexyl and cyclohexyl.

[0266] As used herein, unless expressly stated otherwise, an asterisk symbol "*" represents a bond position at which the correspondingly labeled moiety is attached to another moiety.

[0267] C n The subscript n therein relates to the total number of carbon atoms in the alkyl, arylene, heteroarylene or aryl group, respectively.

[0268] As used herein, the term "aryl" or "arylene" is intended to encompass fused aromatics such as phenyl (C6-aryl), naphthalene, anthracene, phenanthrene, and tetracene. Further encompassed are biphenyls and oligophenyls or polyphenyls, such as terphenyl, phenyl-substituted biphenyls, and phenyl-substituted terphenyls (e.g., tetraphenylbenzene groups). The terms "arylene" and "heteroarylene" refer to groups to which two additional moieties are bonded. As used herein, the terms "aryl group" and "arylene group" refer to groups containing at least one hydrocarbon aromatic moiety, in which all elements of the hydrocarbon aromatic moiety may have p-orbitals that form conjugation (e.g., phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrinyl, fluorenyl, etc.). Further encompassed are spiro compounds in which two aromatic moieties are connected to each other via a spiro atom (e.g., 9,9'-spirobi[9H-fluorenyl]yl). The aryl or arylene group can contain a monocyclic functional group or a fused polycyclic (ie, bond(s) sharing adjacent pairs of carbon atoms) functional group.

[0269] As used herein, the term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced with a heteroatom. The term "heteroaryl" may also refer to an aromatic heterocycle having at least one heteroatom, and all elements of the hydrocarbon heteroaromatic moiety may have p-orbitals that form conjugation. The heteroatom may be selected from N, O, S, B, Si, P, and Se, preferably N, O, and S. The heteroarylene ring may contain at least 1 to 3 heteroatoms. Preferably, the heteroarylene ring may contain at least 1 to 3 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 are diazines, triazines, dibenzofurans, dibenzothiofurans, acridines, benzoacridines, dibenzoacridines, and the like.

[0270] As used herein, the term "alkenyl" refers to the group -CR containing a carbon-carbon double bond. 1 =CR 2 R 3 Refers to...

[0271] As used herein, the term "perhalogenated" refers to a hydrocarbyl group in which all of the hydrogen atoms of the hydrocarbyl group have been replaced by halogen (F, Cl, Br, I) atoms.

[0272] As used herein, the term "alkoxy" refers to a structural fragment of formula -OR, where R is hydrocarbyl, preferably alkyl or cycloalkyl.

[0273] As used herein, the term "thioalkyl" refers to a structural fragment of formula -SR, where R is hydrocarbyl, preferably alkyl, or cycloalkyl.

[0274] C nThe subscript n in -heteroaryl simply refers to the number of carbon atoms excluding the number of heteroatoms. In this context, it is clear that a C heteroarylene group is an aromatic compound containing 3 carbon atoms (such as pyrazole, imidazole, oxazole, thiazole, etc.).

[0275] The term "heteroaryl" as used herein is intended to include pyridine, quinoline, benzoquinoline, quinazoline, benzoquinazoline, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, benzo[4,5]thieno[3,2-d]pyrimidine, carbazole, xanthene, phenoxazine, benzacridine, dibenzoacridine, and the like.

[0276] As used herein, the term single bond refers to a direct bond.

[0277] The term "fluorinated" as used herein refers to a hydrocarbon group in which at least one of the hydrogen atoms contained therein has been replaced with a fluorine atom. A fluorinated group in which all of the hydrogen atoms have been replaced with fluorine atoms is called a perfluorinated group, and is specifically referred to as "fluorinated."

[0278] In the context of this invention, a group is "substituted" with another group (where the other group is a substituent) when one of the hydrogen atoms contained in the group is replaced with another group.

[0279] In the context of the present invention, the expression "between" with respect to a layer that is between two other layers does not exclude the presence of an additional layer that may be disposed between the layer and one of the two other layers. In the context of the present invention, the expression "in direct contact" with respect to two layers that are in direct contact with each other means that no additional layer is disposed between the two layers. A layer that is deposited on top of another layer is considered to be in direct contact with this layer.

[0280] The term "sandwiched contact" refers to an arrangement of three layers in which a middle layer is in direct contact with two adjacent layers.

[0281] For the electron transport stacks of the present invention, the compounds described in the experimental section are most preferred.

[0282] Light-emitting devices can be any device used for illumination, illumination, signaling, or projection. They are correspondingly classified as illumination devices, illumination devices, signaling devices, and projection devices. A light-emitting device typically consists of a light radiation source, a device that transmits the emitted light beam into space in a desired direction, and a housing that joins the components into a single device and protects the radiation source and light transmission system from damage and environmental influences.

[0283] Organic electroluminescent devices (OLEDs) may be bottom-emitting or top-emitting devices. Organic electroluminescent devices (OLEDs) may emit light through a transparent anode or through a transparent cathode.

[0284] Another aspect is directed to a device that includes at least one organic electroluminescent device (OLED).

[0285] A device including an organic light emitting diode is, for example, a display panel or a light emitting panel.

[0286] For purposes of the present invention, the following defined terms shall have these definitions applied, unless a different definition is given in the claims or elsewhere in this specification.

[0287] In the context of this specification, the term "different" or "differs" in relation to matrix materials means that the matrix materials differ in their structural formula.

[0288] The terms "OLED" and "organic light emitting diode" are used interchangeably and have the same meaning. As used herein, the term "organic electroluminescent device" can include both organic light emitting diodes and organic light emitting transistors (OLETs).

[0289] As used herein, "weight percent," "wt.-%," "percent by weight," "% by weight," and variations thereof, refer to a composition, component, substance, or agent by dividing the weight of that component, substance, or agent in each electron transport layer by the total weight of each electron transport layer multiplied by 100. It is understood that the total weight percent amount of all components, substances, and agents in each electron transport layer and electron injection layer is selected not to exceed 100 wt.%.

[0290] As used herein, "volume percent," "vol.-%," "percent by volume," "% by volume," and variations thereof, refer to a composition, component, substance, or agent, by dividing the volume of that component, substance, or agent in each electron transport layer by the total volume of each electron transport layer multiplied by 100. It is understood that the total volume percent amount of all components, substances, and agents in a cathode layer is selected not to exceed 100% by volume.

[0291] In this specification, all numerical values, whether explicitly stated or not, are assumed to be modified by the term "about." As used herein, the term "about" refers to possible variations in quantity. Whether modified by the term "about," the claims include equivalents to the quantities.

[0292] Please note that as used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the content clearly dictates otherwise.

[0293] The terms "free of", "does not contain", "does not comprise" do not exclude impurities, which do not have a technical effect with respect to the objectives achieved by the present invention.

[0294] In the context of this specification, the terms "essentially non-emissive" or "non-emissive" mean that the compound or layer contributes less than 10%, preferably less than 5%, to the visible emission spectrum from the device. The visible emission spectrum is the emission spectrum having wavelengths greater than or equal to about 380 nm and less than or equal to about 780 nm.

[0295] Preferably, the organic semiconductor layer comprising the compound of formula (I) is essentially non-emissive or non-emissive.

[0296] The operating voltage, also known as U, is 10 milliamperes per square centimeter (mA / cm 2 ) is measured in volts (V).

[0297] Candela / ampere efficiency, also known as cd / A efficiency, is 10 milliamperes per square centimeter (mA / cm 2 ) is measured in candela per ampere.

[0298] External quantum efficiency, also called EQE, is measured in percent (%).

[0299] The color space is described by the coordinates CIE-x and CIE-y (International Commission on Illumination 1931). For blue emission, CIE-y is particularly important: a smaller CIE-y indicates a deeper blue. Efficiency values ​​are compared at the same CIE-y.

[0300] The highest occupied molecular orbital, also called the HOMO, and the lowest unoccupied molecular orbital, also called the LUMO, are measured in electron volts (eV).

[0301] The terms "OLED," "organic light emitting diode," "organic light emitting device," "organic optoelectronic device," and "organic light-emitting diode" are used interchangeably and have the same meaning.

[0302] The terms "life-span" and "lifetime" are used interchangeably and have the same meaning.

[0303] The anode and cathode may be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer.

[0304] Room temperature, also known as ambient temperature, is 23°C.

[0305] BRIEF DESCRIPTION OF THE DRAWINGS These and / or other aspects and advantages of the present invention will become apparent and will be more readily understood from the following description of exemplary embodiments taken in conjunction with the accompanying drawings: FIG. 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; FIG. 2 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0306] Detailed Description Reference will now be made in detail to the exemplary embodiments of the invention, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. For the purposes of explaining aspects of the invention, the exemplary embodiments will now be described by reference to the drawings.

[0307] As used herein, when a first element is said to be formed or disposed "on" or "onto" a second element, the first element can be disposed directly on the second element, or one or more other elements can be disposed between them. When a first element is said to be formed or disposed "directly on" or "directly onto" a second element, no other elements are disposed between them.

[0308] 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes an opaque substrate 110, an anode 120, a hole-injection layer (HIL) 130, a hole-transport layer (HTL) 140, an emissive layer (EML) 150, and an electron-transport stack (ETL) 160 containing a first electron-transport layer 161 and a second electron-transport layer 162. The electron-transport layer (ETL) 160 is formed on the EML 150. An electron-injection layer (EIL) 180 is disposed on the electron-transport layer (ETL) 160. A cathode 190 is disposed directly on the electron-injection layer (EIL) 180.

[0309] 2 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. FIG. 2 differs from FIG. 1 in that the OLED 100 of FIG. 2 includes an electron blocking layer (EBL) 145.

[0310] Referring to FIG. 2, OLED 100 includes an opaque substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, an electron transport stack (ETL) 160 containing a first electron transport layer 161 and a second electron transport layer 162, an electron injection layer (EIL) 180, and a cathode electrode 190.

[0311] 1 and 2, an encapsulation layer may be further formed on the cathode electrode 190 to encapsulate the OLED 100 and the OLED 200. Various other modifications may also be applied.

[0312] One or more exemplary embodiments of the present invention will now be described in detail with reference to the following examples, which are not intended to limit the scope or spirit of the one or more exemplary embodiments of the present invention.

[0313] Detailed Description [Dipole moment] Dipole moments of molecules containing N atoms

[0314]

number

[0315] is given by the following formula:

[0316]

number

[0317] During the ceremony,

[0318]

number

[0319] are the partial charges and position of atom i in the molecule.

[0320] The dipole moment is determined by semi-empirical molecular orbital methods.

[0321] 6-31G in the gas phase as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * The geometry of a molecular structure is optimized by applying the hybrid functional B3LYP with basis set. If two or more conformations are feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule.

[0322] [Calculated values ​​of HOMO and LUMO] The HOMO and LUMO are calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure and the HOMO and LUMO energy levels are calculated using the 6-31G * The conformation is determined by applying the hybrid function B3LYP with the basis set. If more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0323] [OLED performance measurement] To evaluate the performance of the OLED devices, the current efficiency is measured at 20°C. The current-voltage characteristics are determined using a Keithley 2635 source-measure unit by supplying a voltage in V and measuring the current in mA through the device being tested. The voltage applied to the device is varied in 0.1 V increments from 0 V to 10 V. Similarly, the luminance-voltage characteristics and CIE coordinates are measured in cd / m for each voltage value using an Instrument Systems CAS-140CT array analyzer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 Determined by measuring the luminance at 10 mA / cm 2 The cd / A efficiency at is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[0324] If applicable, the device life LT is measured under ambient conditions (20°C) and 30 mA / cm 2 can be measured using a Keithley 2400 source meter and recorded in hours.

[0325] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the brightness of the device has decreased to 97% of its initial value.

[0326] The increase in operating voltage ΔU is used as a measure of the device's operating voltage stability. This increase is determined by subtracting the operating voltage at the start of operation from the operating voltage after 50 hours during the LT measurement.

[0327] ΔU = [U(50h) - U(0h)] The smaller the value of ΔU, the better the operating voltage stability.

[0328] General Procedure for Fabrication of OLEDs For the top-emission OLED device, a substrate having dimensions of 150 mm × 150 mm × 0.7 mm was ultrasonically cleaned in a spin-wash dryer with a 2% aqueous solution of Deconex FPD 211 for 7 minutes, then with pure water for 5 minutes, and then dried for 15 minutes. -5 ~10 -7 The evaporation was carried out at a pressure of 1000 mbar.

[0329] HT-1 and D-1 were then co-evaporated onto the anode to form the HIL, HT-1 was then vacuum-evaporated onto the HIL to form the HTL, and HT-2 was then vacuum-evaporated onto the HTL to form the electron blocking layer (EBL).

[0330] Then, an emitting layer was formed on the EBL by co-evaporation of host-1 and emitter-1.

[0331] Next, a compound of formula (I) was vacuum-deposited on the light-emitting layer to form a first electron-transporting layer. Next, for Examples OLED-1 to OLED-12, a compound of formula (II) was vapor-deposited on the first electron-transporting layer to form a second electron-transporting layer. For Comparative OLED Examples, a second electron-transporting layer was formed on the first electron-transporting layer by vapor-depositing Compound C-3.

[0332] For Examples OLED-13 to OLED-20, a premix compound of the compound of formula (II) and the compound (III) was vapor-deposited to form a second electron-transporting layer on the first electron-transporting layer.

[0333] An electron injection layer was then formed on the second electron transport layer as a bilayer by first evaporating LiQ and then Yb.

[0334] Then, Ag:Mg was added to 10 -7 The cathode was formed by evaporation at a rate of 0.01-1 Å / s at mbar.

[0335] A capping layer of HT-3 was formed on the cathode.

[0336] The stack details for a top-emitting OLED device are shown below. A slash " / " separates the individual layers. Layer thicknesses are indicated in square brackets [...] and mixture ratios in weight percent are indicated in parentheses (...): Stack details used in the OLED device examples in Table 6: Ag [100 nm] / HT-1:NDP-9 (weight % 92:8) [10 nm] / HT-1 [130 nm] / HT-2 [5 nm] / H09:BD200 (weight % 97:3) [20 nm] / compound of formula (I) [5 nm] / compound of formula (II) or C-3 [30 nm] / LiQ [1 nm] / Yb [2 nm] / Ag:Mg (weight % 90:10) [13 nm] / HT-3 [75 nm] Stack details used in the OLED device examples in Table 7: Ag [100 nm] / HT-1:NDP-9 (weight % 92:8) [10 nm] / HT-1 [130 nm] / HT-2 [5 nm] / H09:BD200 (weight % 97:3) [20 nm] / compound of formula (I) [5 nm] / compound of formula (II): compound of formula (III) (weight % 30:70) [30 nm] / LiQ [1 nm] / Yb [2 nm] / Ag:Mg (weight % 90:10) [13 nm] / HT-3 [75 nm]

[0337] [Table 6]

[0338] [Table 7]

[0339] [Table 8]

[0340] Examples 15, 16, 19 and 20 show that when compound (III) is used in the second electron transport layer, the cd / A efficiency is further increased at similar or lower voltages.

[0341] The features disclosed in the above description and in the dependent claims may, both separately and in any combination thereof, be material for realising the aspects of the invention as set out in the independent claims in their various forms. [Brief explanation of the drawings]

[0342] [Figure 1] 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. [Figure 2] 1 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

Claims

1. an opaque substrate, an anode, a cathode, an emissive layer, an electron injection layer, and an electron transport stack; the electron transport stack is disposed between the light-emitting layer and the electron injection layer; the electron transport stack includes a first electron transport layer and a second electron transport layer; the first electron transport layer comprises a compound of formula (I), (Ar １ -A ｃ ) ａ -X ｂ (I); a and b are independently 1 or 2; c is independently 0 or 1; Ar １ is C ６ ~C ６０ Aryl or C ２ ~C ４２ heteroaryl; Here, Ar １ Each is C ６ ~C １２ Aryl, 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 perdeuterated C １ ~C ６ Alkyl, partially deuterated or perdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R １０ ) ２ wherein 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 independently selected from alkoxy; Here, Ar １ C above ６ ~C １２ Aryl substituents, respectively, and Ar １ C above ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ optionally substituted with alkyl or halogen; A is C ６ ~C ３０ aryl; Here, each 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 wherein 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 independently selected from alkoxy; Here, C on A ６ ~C １２ Each aryl substituent is C １ ~C ４ optionally substituted with alkyl or halogen; X is C ２ ~C ４２ Heteroaryl and C ６ ~C ６０ aryl; where each X is C ６ ~C １２ Aryl, 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 perdeuterated C １ ~C ６ Alkyl, partially deuterated or perdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R １０ ) ２ wherein 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 independently selected from alkoxy; Here, C on X ６ ~C １２ Each of the aryl substituents and C on X ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ optionally substituted with alkyl or halogen; The molecular dipole moment of the compound of formula (I) is 0D or more and 4D or less; the second electron transport layer comprises a 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 is C ２ ~C ４２ Heteroaryl and C ６ ~C ６０ aryl; Here, Ar ２ Each is C ６ ~C １２ Aryl, 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 perdeuterated C １ ~C ６ Alkyl, partially deuterated or perdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R １０ ) ２ wherein Y is selected from O, S, or Se; and R １０ is independent, 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 alkoxy; Here, Ar ２ C above ６ ~C １２ Aryl substituents, respectively, and Ar ２ C above ３ ~C １１ Each heteroaryl substituent is C １ ~C ４ optionally substituted with alkyl or halogen; Z is C ６ ~C ３０ 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 perdeuterated C １ ~C ６ Alkyl, partially deuterated or perdeuterated C １ ~C ６ Alkoxy, halogen, CN or PY(R １０ ) ２ wherein 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 independently selected from alkoxy; Here, C on Z ６ ~C １２ Each aryl substituent is C １ ~C ４ optionally substituted with alkyl or halogen; G is selected such that the dipole moment of compound G-phenyl is greater than or equal to 1D and less than or equal to 7D; the first electron transport layer and the second electron transport layer do not include an electrical dopant; It is excluded that the compound of formula (II) is a compound of the following formula: 【Chemistry 1】 the electron injection 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; Organic light-emitting diode.

2. Ar １ are independently selected from the group consisting of phenyl, naphthyl, anthracenyl, fluoranthenyl, xanthenyl, spiro-xanthenyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having the formula (IIa), 【Chemistry 2】 During the ceremony, The asterisk symbol "*" represents the attachment point for attaching the group of formula (IIa) to A; R １ ~R ５ is H, C ６ ~C １２ Aryl and C ４ ~C １０ independently selected from the group consisting of heteroaryl; The organic light-emitting diode of claim 1 .

3. A is selected from the group consisting of phenylene, naphthylene, biphenylene, and terphenylene, each of which may be substituted or unsubstituted; The organic light-emitting diode of claim 1 .

4. X is independently selected from the group consisting of triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenanthrolinyl, and dinaphthofuranyl, each of which may be substituted or unsubstituted; The organic light-emitting diode of claim 1 .

5. Ar ２ are independently selected from the group consisting of pyridinyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzacridinyl, dibenzoacridinyl, fluoranthenyl, anthracenyl, naphthyl, triphenylenyl, phenathrolinyl, and dinaphthofuranyl, each of which may be substituted or unsubstituted; The organic light-emitting diode of claim 1 .

6. G is selected from the group consisting of dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, nitrile, benzonitrile, nicotinonitrile, amido-yl, carbamido-yl and C ２ ~C １７ selected from the group consisting of heteroaryl; Each G is the dialkylphosphinyl, diarylphosphinyl, alkylarylphosphinyl, nitrile, benzonitrile, nicotinonitrile, amido-yl, carbamido-yl or C ２ ~C １７ The heteroaryl may include one or more substituents attached thereto, wherein said one or more substituents are selected from the group consisting of phenyl, methyl, ethyl, and pyridyl. The organic light-emitting diode of claim 1 .

7. G is independently 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 organic light-emitting diode of claim 1 .

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

9. The compound of formula (II) is selected from B-1 to B-26. 【Chemistry 4】 【change】 【change】 The organic light-emitting diode of claim 1 .

10. the second electron transport layer further comprises a compound (III), wherein the compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; The organic light-emitting diode of claim 1 .

11. The compound (III) contains 1 to 5 heteroaromatic rings.

11. The organic light-emitting diode of claim 10.

12. When 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 a heteroatom.

11. The organic light-emitting diode of claim 10.

13. the first electron transport layer and the second electron transport layer are in direct contact with each other; The organic light-emitting diode of claim 1 .

14. the second electron transport layer is in direct contact with the electron injection layer; The organic light-emitting diode of claim 1 .

15. The compound (II) is not contained in the electron injection layer. The organic light-emitting diode of claim 1 .

16. A device comprising an organic light-emitting diode according to any one of claims 1 to 15, The device is a display device or a light-emitting device. Device.

17. A compound having the structure of formula A11, A12, A14, A16, A18, A22, A24, A25, or A27. 【Transformation 5】 【change】

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