Organic light emitting diode comprising organometallic compound and multiple types of host materials

Abstract

The present disclosure relates to an organic light-emitting diode comprising an organometallic compound and a plurality of types of host materials, and in particular, to a light-emitting layer and an organic light-emitting diode comprising the same, and can achieve characteristics of the organic light-emitting diode such as high luminous efficiency and long lifespan, the light-emitting layer comprising a dopant material and a host material, the dopant material includes an organometallic compound represented by Chemical Formula 1, and the host material includes a compound represented by Chemical Formula 2 and a compound represented by Chemical Formula 3.

Description

Technical Field

[0001] The present disclosure relates to organic light emitting diodes including organometallic compounds and various types of host materials. Background Art

[0002] According to applications in various fields, interest in display devices is increasing. As one of the display devices, technology of organic light emitting display devices including organic light emitting diodes (OLEDs) is rapidly developing.

[0003] OLED is an element for emitting the energy of excitons as light after electrons and holes are paired to form excitons when charges are injected into a light-emitting layer formed between an anode and a cathode. Compared with conventional display technologies, OLED can achieve low voltage, consume relatively little power, have excellent color, can be applied to flexible substrates to be used variously, and can allow the size of the display device to be freely adjusted.

[0004] Compared with liquid crystal display (LCD) devices, OLEDs can have wide viewing angles and high contrast, and do not require backlight, making them lightweight and ultra-thin. OLEDs are formed by arranging a plurality of intermediate layers such as a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. between a cathode (electron injection electrode) and an anode (hole injection electrode).

[0005] In the structure of OLED, when a voltage is applied between two electrodes, electrons and holes are injected from the cathode and the anode, respectively, and excitons generated by the light-emitting layer fall to a ground state to emit light.

[0006] The organic materials used in OLEDs can be roughly divided into light-emitting materials and charge transport materials. The light-emitting material is an important factor in determining the luminous efficiency of OLEDs, and the light-emitting material should have high quantum efficiency, excellent electron and hole mobility, and be uniformly and stably present in the light-emitting layer. The light-emitting material is divided into light-emitting materials such as blue, red, and green according to the colored light, and is used as a host and a dopant to improve the color purity and improve the luminous efficiency as a colored material through energy transfer.

[0007] In the case of fluorescent materials, although only about 25% of singlet states among excitons formed in the light-emitting layer are used to generate light and 75% of triplets are mostly lost as heat, phosphorescent materials have a light-emitting mechanism that converts both singlet states and triplets into light.

[0008] To date, organometallic compounds have been used as phosphorescent materials used in OLEDs. There is still a technical need to improve the performance of OLEDs by obtaining highly efficient phosphorescent dopant materials and applying hosts with optimal photophysical properties to improve the efficiency and life of the element compared to conventional OLEDs. Summary of the invention

[0009] Accordingly, the present disclosure is directed to providing an organic light emitting diode in which an organic metal compound capable of improving driving voltage, efficiency, and lifespan and various types of host materials are applied to an organic light emitting layer.

[0010] The purpose of the present disclosure is not limited to the above-mentioned purpose, and other purposes and advantages not mentioned in the present disclosure can be understood by the following description, and can be more clearly understood by the embodiments of the present disclosure. In addition, it can be easily seen that the purposes and advantages of the present disclosure can be achieved by the means described in the claims and their combinations.

[0011] To achieve this object, an embodiment of the present disclosure may provide an organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises a light emitting layer, and the light emitting layer comprises a dopant material and a host material, the dopant material comprises an organic metal compound represented by the following Chemical Formula 1, and the host material comprises a mixture of a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3:

[0012] [Chemical formula 1]

[0013]

[0014] In Chemical Formula 1,

[0015] X is at least one selected from oxygen (O), sulfur (S) and selenium (Se),

[0016] R1 to R6 are each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, nitrile, isonitrile, thiol, phosphine, a group formed by connecting two or more of the above groups, and combinations thereof,

[0017] R7 and R8 are each independently at least one selected from the group consisting of hydrogen, deuterium, C1-C6 linear alkyl, C3-C6 branched alkyl and C3-C6 cycloalkyl,

[0018] Optionally, at least one of R1 to R8 may be partially or fully deuterated,

[0019] a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 2 to 4, the plurality of R1s or the plurality of R2s are the same or different from each other,

[0020] c and f are each independently an integer of 0 to 3, and when c and f are each independently an integer of 2 or 3, a plurality of R3 or a plurality of R6 are the same or different from each other,

[0021] d is an integer from 0 to 2, and when d is an integer of 2, the plurality of R4 are the same as or different from each other,

[0022] e is an integer from 0 to 5, and when e is an integer from 2 to 5, the plurality of R5 are the same as or different from each other, and

[0023] m is an integer of 1 to 8, and when m is 2 or more, a plurality of R7 are the same as or different from each other, and a plurality of R8 are the same as or different from each other, and

[0024] n is an integer from 0 to 2,

[0025] [Chemical formula 2]

[0026]

[0027] In chemical formula 2,

[0028] R 9a and R 9b are each independently one selected from the following: hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylamino, heteroaryl, and a group formed by connecting two or more of the above groups, or R 9a and R 9b Bonded to each other to form spirofluorene,

[0029] R 10 and R 11a To R 11c are each independently one selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, amino, arylamino, aryl, heteroaryl, and a group formed by linking two or more of the above groups,

[0030] L1 is one selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a divalent naphthylene group, a divalent dibenzofuranyl group, and a divalent dibenzothienyl group,

[0031] Ar1 and Ar2 are each independently one selected from the group consisting of an aryl group, an arylamino group, a heteroaryl group, and a group formed by connecting two or more of the above groups, and when Ar1 and Ar2 are the group formed by connecting two or more of the above groups, two or more of the groups are connected by a single bond, an alkylene group, -O- or an alkyleneoxy group, and

[0032] Optionally, Ar1 and / or Ar2 are each substituted by Ra substituted, and when there is R a When R a are each independently at least one selected from the group consisting of deuterium, halogen, alkyl, alkoxy, thioalkyl, alkylsilyl, a group formed by connecting two or more of the above groups, and a combination thereof,

[0033] [Chemical formula 3]

[0034]

[0035] In chemical formula 3,

[0036] N-Het is a substituted or unsubstituted monocyclic or polycyclic heteroaryl containing one or more nitrogen,

[0037] L2 is one selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C60 heteroarylene group,

[0038] g is an integer from 1 to 3, and when g is 2 or more, L2 are the same as or different from each other,

[0039] R 12 To R 21 each independently represents one selected from the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted phosphine oxide, and substituted or unsubstituted amine, and

[0040] Optionally, R 12 To R 21 Two or more adjacent groups in the R 22 The ring structure of a substituted C6-C60 aryl group, or an unsubstituted or R 22 The ring structure of the substituted C2-C60 heteroaryl group,

[0041] When there is R 22 When R 22 are each independently at least one selected from the group consisting of a C1-C20 alkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group, and

[0042] h and i are each an integer from 0 to 3, and when h is 2 or greater, R20 are the same as or different from each other, and when i is 2 or greater, R 21 The same as or different from each other.

[0043] According to another aspect of the present disclosure, an organic light emitting diode can be provided, which includes: a first electrode; a second electrode facing the first electrode; and one or more light emitting portions positioned between the first electrode and the second electrode, wherein at least one of the light emitting portions includes a green phosphorescent light emitting layer, the green phosphorescent light emitting layer includes a dopant material and a host material, the dopant material includes an organic metal compound represented by the following Chemical Formula 1, and the host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3, and the definitions of Chemical Formulas 1 to 3 are the same as those defined in one aspect of the present disclosure. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] Figure 1 FIG. 1 is a cross-sectional view schematically showing an organic light emitting diode according to an embodiment of the present disclosure.

[0045] Figure 2 FIG. 1 is a cross-sectional view schematically showing an organic light emitting diode having a series structure with two light emitting parts according to an embodiment of the present disclosure.

[0046] Figure 3 FIG. 1 is a cross-sectional view schematically showing an organic light emitting diode having a series structure and three light emitting portions according to an embodiment of the present disclosure.

[0047] Figure 4 is a cross-sectional view schematically showing an OLED display device to which an organic light emitting diode according to an exemplary embodiment of the present disclosure is applied. DETAILED DESCRIPTION

[0048] The above-mentioned objects, features and advantages will be described in detail below with reference to the accompanying drawings, and thus those skilled in the art to which the present disclosure belongs will be able to easily implement the technical spirit of the present disclosure. When describing the present disclosure, when it is determined that the detailed description of the known technology related to the present disclosure may unnecessarily obscure the gist of the present disclosure, its detailed description will be omitted. Hereinafter, exemplary embodiments according to the present disclosure will be described in detail with reference to the accompanying drawings. In the accompanying drawings, the same reference numerals are used to represent the same or similar parts.

[0049] In the specification, other parts may be added when the terms "including", "having", "consisting of", "arranged", "set", etc. are used unless "only" is used. Unless otherwise specifically stated, when a component is expressed in the singular, this includes the case where the component is provided as plural components.

[0050] In interpreting components in the specification, even when there is no separate explicit description, the components should be interpreted as including the error range.

[0051] In the specification, the arrangement of any component on the "upper (or lower)" of a component or "above (or below)" the component may mean not only that the arbitrary component is disposed in contact with the upper surface (or lower surface) of the component, but also that another component may be interposed between the component and any component disposed above (or below) the component.

[0052] As used herein, the term "halo" or "halogen" includes fluorine, chlorine, bromine and iodine.

[0053] The term "alkyl" used herein means both linear alkyl and branched alkyl. Unless otherwise indicated, linear alkyl contains 1 to 60 carbon atoms, 1 to 30 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms, and branched alkyl contains 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 20 carbon atoms, or 3 to 10 carbon atoms, and may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc., and in addition, alkyl may be substituted arbitrarily.

[0054] The term "cycloalkyl" used herein means a cyclic alkyl group. Unless otherwise specified, the cycloalkyl group contains 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 20 carbon atoms, or 3 to 10 carbon atoms, and may include cyclopropyl, cyclopentyl, cyclohexyl, etc., and in addition, the cycloalkyl group may be arbitrarily substituted.

[0055] The term "alkenyl" used herein means both linear alkenyl and branched alkenyl. Unless otherwise specified, alkenyl contains 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms, and in addition, alkenyl can be arbitrarily substituted.

[0056] The term "cycloalkenyl" as used herein refers to a cyclic alkenyl group. Unless otherwise specified, the cycloalkenyl group contains 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 20 carbon atoms, or 3 to 10 carbon atoms, and further, the cycloalkenyl group may be arbitrarily substituted.

[0057] The term "alkynyl" as used herein refers to both linear alkynyl and branched alkynyl. Unless otherwise indicated, alkynyl contains 2 to 60 carbon atoms, 2 to 30 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms. In addition, alkynyl can be arbitrarily substituted.

[0058] The term "cycloalkynyl" as used herein refers to a cyclic alkynyl group. Unless otherwise specified, the cycloalkynyl group contains 3 to 60 carbon atoms, 3 to 30 carbon atoms, 3 to 20 carbon atoms, or 3 to 10 carbon atoms, and the cycloalkynyl group may be arbitrarily substituted.

[0059] As used herein, the terms "aralkyl" and "arylalkyl" are used interchangeably and refer to an alkyl group having an aromatic group as a substituent, and unless otherwise specified, the aralkyl group contains 7 to 60 carbon atoms, 7 to 30 carbon atoms, or 7 to 20 carbon atoms, and further, the aralkyl group (arylalkyl group) may be arbitrarily substituted.

[0060] The terms "aryl" and "aromatic group" used herein may include conjugated structures and may include monocyclic groups and polycyclic groups. Polycyclic may include "condensed rings", which are two or more rings in which two adjacent rings share two carbons. Unless otherwise indicated, aryl contains 6 to 60 carbon atoms, 6 to 30 carbon atoms, or 6 to 20 carbon atoms. Monocyclic aryl includes phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl includes naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, etc., but is not limited thereto. In addition, aryl may be substituted arbitrarily. The above description of aryl may be applied to arylidene, except that arylidene is a divalent group.

[0061] The term "heterocyclic radical" used herein means that one or more of the carbon atoms constituting aryl, cycloalkyl, cycloalkenyl, cycloalkynyl, aralkyl (arylalkyl), arylamino etc. are replaced by heteroatoms such as oxygen (O), nitrogen (N), sulphur (S), etc., and with reference to the above definition, including heteroaryl, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, heteroaralkyl (heteroarylalkyl), heteroarylamino etc., and unless otherwise specified, heteroaryl contains 2 to 60 carbon atoms, 2 to 30 carbon atoms or 2 to 20 carbon atoms. The example of heteroaryl includes thienyl, furyl, pyridyl, pyrimidyl, triazine, quinolyl, quinazolinyl, quinoxalinyl, benzothienopyrimidyl, benzofuranpyrimidyl, carbazolyl, N-phenylcarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl etc., but is not limited thereto. In addition, heterocyclic radical can be substituted arbitrarily. The above description of heteroaryl can be applied to heteroarylene, except that the heteroarylene is a divalent group.

[0062] Unless otherwise specified, the term "carbocycle" used herein may be used as a term including all of "cycloalkyl", "cycloalkenyl" and "cycloalkynyl" which are alicyclic ring groups, and "aryl (aromatic group)" which is an aromatic ring group.

[0063] The terms "heteroalkyl", "heteroalkenyl", "heteroalkynyl" and "heteroaralkyl (heteroarylalkyl)" as used herein mean that one or more of the carbon atoms constituting the corresponding "alkyl", "alkenyl", "alkynyl" and "aralkyl (heteroarylalkyl)" are replaced by heteroatoms such as oxygen (O), nitrogen (N) and sulfur (S), and further, heteroalkyl, heteroalkenyl, heteroalkynyl and heteroaralkyl (heteroarylalkyl) may be arbitrarily substituted.

[0064] The terms "alkylamino", "aralkylamino", "arylamino" and "heteroarylamino" as used herein mean that an amine group is substituted with an alkyl group, an aralkyl group, an aryl group and a heteroaryl group (which is a heterocyclic ring), and include all primary amines, secondary amines and tertiary amines, and further, the alkylamino group, the aralkylamino group, the arylamino group and the heteroarylamino group may be arbitrarily substituted.

[0065] The terms "alkylsilyl", "arylsilyl", "alkoxy", "aryloxy", "alkylthio" and "arylthio" mean that a silyl group, an oxy group or a thio group is substituted with an alkyl group and an aryl group, respectively, and further, the alkylsilyl group, the arylsilyl group, the alkoxy group, the aryloxy group, the alkylthio group and the arylthio group may be arbitrarily substituted.

[0066] The term "substituted" as used herein means that instead of a hydrogen atom (H) being bonded to a carbon atom, another substituent is bonded to the corresponding carbon atom. The substituent used in the case of "substituted" may have a single substituent or a plurality of substituents. When there are a plurality of substituents, each substituent may be the same or different from each other.

[0067] Unless otherwise specified herein, substituents may be selected from: deuterium; halogen; alkyl; cycloalkyl; heteroalkyl; arylalkyl; alkoxy; aryloxy; amino; silyl; alkenyl; cycloalkenyl; heteroalkenyl; alkynyl; aryl; heteroaryl; acyl; carboxylic acid; ester; nitrile; isonitrile; thiol; sulfinyl; sulfonyl; phosphino; and groups formed by linking two or more of the above groups, and the substituents may be partially or fully deuterated.

[0068] As used herein, "deuterated" may mean substitution of deuterium in place of light hydrogen in a compound.

[0069] The term "combinations thereof" in the definition of substituents means that a plurality of substituents may be present and the plurality of substituents are defined as combinations from the defined list.

[0070] Unless otherwise specified herein, the position of substitution is not limited as long as it is a position where a hydrogen atom is substituted (ie, a position where a substituent can substitute), and when two or more substituents are present, the substituents may be the same as or different from each other.

[0071] Unless otherwise stated, objects and substituents as defined herein may be the same as or different from each other.

[0072] Hereinafter, the structure of an organic metal compound and an organic light emitting diode including the same according to the present disclosure will be described in detail.

[0073] Typically, an organic metal compound is used as a dopant in a phosphorescent light-emitting layer, for example, a structure such as 2-phenylpyridine is considered to be the main ligand structure of the organic metal compound. However, since conventional luminescent dopants have limitations in improving the efficiency and life of organic light-emitting diodes, it is necessary to develop new luminescent dopant materials. The present disclosure is completed by experimentally confirming that by mixing a hole transport type host and an electron transport type host as host materials with a dopant material, the efficiency and life of the organic light-emitting diode can be further improved and the driving voltage can be reduced, thereby improving the characteristics of the organic light-emitting diode.

[0074] Specifically, referring to an embodiment according to the present disclosure Figure 1 , an organic light emitting diode 100 may be provided, which includes a first electrode 110, a second electrode 120 facing the first electrode 110, and an intermediate layer 130 disposed between the first electrode 110 and the second electrode 120. The intermediate layer 130 may include a light emitting layer 160, the light emitting layer 160 may include a dopant material 160' and host materials 160" and 160"', and include an organic metal compound represented by the following Chemical Formula 1 as the dopant material 160', and the host material may include the following two types: a compound represented by the following Chemical Formula 2 as a hole transport type host 160" and a compound represented by the following Chemical Formula 3 as an electron transport type host 160"'.

[0075] [Chemical formula 1]

[0076]

[0077] In Chemical Formula 1,

[0078] X is at least one selected from oxygen (O), sulfur (S) and selenium (Se),

[0079] R1 to R6 are each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, nitrile, isonitrile, thiol, phosphine, a group formed by connecting two or more of the above groups, and combinations thereof,

[0080] R7 and R8 are each independently at least one selected from the group consisting of hydrogen, deuterium, C1-C6 linear alkyl, C3-C6 branched alkyl and C3-C6 cycloalkyl,

[0081] Optionally, at least one of R1 to R8 may be partially or fully deuterated,

[0082] a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 2 to 4, the plurality of R1s or the plurality of R2s are the same or different from each other,

[0083] c and f are each independently an integer of 0 to 3, and when c and f are each independently an integer of 2 or 3, a plurality of R3 or a plurality of R6 are the same or different from each other,

[0084] d is an integer from 0 to 2, and when d is an integer of 2, the plurality of R4 are the same as or different from each other,

[0085] e is an integer from 0 to 5, and when e is an integer from 2 to 5, the plurality of R5 are the same as or different from each other, and

[0086] m is an integer of 1 to 8, and when m is 2 or more, a plurality of R7 are the same as or different from each other, and a plurality of R8 are the same as or different from each other, and

[0087] n is an integer from 0 to 2,

[0088] [Chemical formula 2]

[0089]

[0090] In chemical formula 2,

[0091] R 9a and R 9b are each independently one selected from the following: hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylamino, heteroaryl, and a group formed by connecting two or more of the above groups, or R 9a and R 9b Bonded to each other to form spirofluorene,

[0092] R 10 and R 11a To R 11c are each independently one selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, amino, arylamino, aryl, heteroaryl, and a group formed by linking two or more of the above groups,

[0093] L1 is one selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a divalent naphthylene group, a divalent dibenzofuranyl group, and a divalent dibenzothienyl group,

[0094] Ar1 and Ar2 are each independently one selected from the group consisting of an aryl group, an arylamino group, a heteroaryl group, and a group formed by connecting two or more of the above groups, and when Ar1 and Ar2 are the group formed by connecting two or more of the above groups, two or more of the groups are connected by a single bond, an alkylene group, -O- or an alkyleneoxy group, and

[0095] Optionally, Ar1 and / or Ar2 may each be substituted by a substituent R a substituted, and when there is R a When R a are each independently at least one selected from the group consisting of deuterium, halogen, alkyl, alkoxy, thioalkyl, alkylsilyl, a group formed by connecting two or more of the above groups, and a combination thereof,

[0096] [Chemical formula 3]

[0097]

[0098] In chemical formula 3,

[0099] N-Het is a substituted or unsubstituted monocyclic or polycyclic heteroaryl containing one or more nitrogen,

[0100] L2 is one selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C60 heteroarylene group,

[0101] g is an integer from 1 to 3, and when g is 2 or more, L2 are the same as or different from each other,

[0102] R 12 To R 21 each independently represents one selected from the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted phosphine oxide, and substituted or unsubstituted amine, and

[0103] Optionally, R 12 To R21 Two or more adjacent groups in R may be bonded to form an unsubstituted or substituted 22 The ring structure of a substituted C6-C60 aryl group, or an unsubstituted or R 22 The ring structure of the substituted C2-C60 heteroaryl group, for example, R 12 To R 21 Two or more adjacent groups in the formula may be bonded to form a carbazole or dibenzofuran moiety fused to the carbazole or dibenzofuran moiety in Formula 3. Wherein Z is one selected from the following: NR 23 , C(R 23 )2, oxygen (O) and sulfur (S), and R 23 may be independently selected from C1-C20 alkyl, C6-C30 aryl and C3-C30 heteroaryl,

[0104] When there is R 22 When R 22 are each independently at least one selected from the group consisting of a C1-C20 alkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group, and

[0105] h and i are each an integer from 0 to 3, and when h is 2 or greater, R 20 are the same as or different from each other, and when i is 2 or greater, R 21 The same as or different from each other.

[0106] According to one embodiment of the present disclosure, m in Chemical Formula 1 may be 1 or more, for example, an integer of 1 to 3, for example, an integer of 1 or 2.

[0107] According to one embodiment of the present disclosure, R1 and R2 may each independently be at least one selected from the group consisting of deuterium, a C1-C10 alkyl group, a C6-C30 aryl group, a C3-C30 heteroaryl group, and a C7-C40 arylalkyl group.

[0108] According to one embodiment of the present disclosure, R1 and R2 may each independently be a C1-C3 alkyl group, wherein R1 and R2 may be substituted with deuterium.

[0109] According to one embodiment of the present disclosure, R3 may be a C1-C3 linear alkyl group, wherein R3 may be substituted with deuterium.

[0110] According to one embodiment of the present disclosure, R4 may not exist and (R4) d The d in can be 0.

[0111] According to one embodiment of the present disclosure, R5 may not exist and (R5) e Where e can be 0, or (R5) eThe e in can be 1 or 2.

[0112] According to one embodiment of the present disclosure, when (R5) in Chemical Formula 1 e When e in is 1 or 2, R5 may be at least one selected from the group consisting of deuterium, a C1-C10 linear alkyl group, and a C3-C10 branched alkyl group, and R5 may be substituted with deuterium.

[0113] According to one embodiment of the present disclosure, R6 may not exist and (R6) f The f in can be 0.

[0114] According to one embodiment of the present disclosure, R7 and R8 define an aralkyl group bonded to the pyridine portion in Chemical Formula 1, and preferably, each independently can be hydrogen, deuterium, a C1-C3 linear alkyl group, and a C3-C6 branched alkyl group, and optionally, the C1-C3 linear alkyl group or the C3-C6 branched alkyl group selected as R7 and R8 can each independently be substituted by deuterium.

[0115] According to one embodiment of the present disclosure, the organometallic compound represented by Chemical Formula 1 may be one of the following compounds GD1 to GD20, but is not limited thereto as long as it is included in the chemical formula

[0116] It can be within the constraints of Formula 1.

[0117]

[0118]

[0119]

[0120] According to one embodiment of the present disclosure, R in Chemical Formula 2 10 and R 11a To R 11c may each independently be hydrogen or deuterium.

[0121] According to one embodiment of the present disclosure, L1 in Chemical Formula 2 may be a single bond or a cyclic group, and the cyclic group may be one selected from the following: a phenylene group, a biphenylene group, a divalent naphthylene group, a divalent dibenzofuranyl group, and a divalent dibenzothiophenyl group, but is not necessarily limited thereto. In this case, when L1 is not a single bond, the position of L1 bonded while connecting the fluorene moiety to the nitrogen (N) of the amino group is not particularly limited.

[0122] According to one embodiment of the present disclosure, L1 in Chemical Formula 2 may be one selected from a single bond and a phenylene group.

[0123] An exemplary structure of L1 in Chemical Formula 2 is as follows, but is not limited thereto.

[0124]

[0125] According to one embodiment of the present disclosure, Ar1 and Ar2 in Chemical Formula 2 may each independently be one selected from the following: an aryl group, an arylamino group, a heteroaryl group, and a composite structure of an aryl group and a heteroaryl group. In this case, in the composite group of an aryl group and a heteroaryl group, the aryl group and the heteroaryl group may be bonded by a single bond, an alkylene group, -O- or an alkyleneoxy group. Optionally, at least one hydrogen in each of Ar1 and / or Ar2 may be substituted by a substituent R a Replace, and R a Each may be independently one selected from the group consisting of deuterium, a halogen, an alkyl group, an alkoxy group, a thioalkyl group, an alkylsilyl group, and a group formed by linking two or more of the above groups.

[0126] Exemplary structures of Ar1 and Ar2 in Chemical Formula 2 are as follows, but are not limited thereto.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] According to one embodiment of the present disclosure, the compound represented by Chemical Formula 2 may be one of the following compounds GHH1 to GHH30, but is not limited thereto as long as it is included in the definition of Chemical Formula 2.

[0133]

[0134]

[0135]

[0136] According to one embodiment of the present disclosure, N-Het of Chemical Formula 3 may be a substituted or unsubstituted triazine group.

[0137] According to one embodiment of the present disclosure, N—Het in Chemical Formula 3 may be a triazine group mono-substituted or di-substituted with a substituent selected from a phenyl group, a biphenyl group, and a naphthyl group.

[0138] According to one embodiment of the present disclosure, L2 in Chemical Formula 3 may be a single bond or a phenylene group.

[0139] According to one embodiment of the present disclosure, the compound represented by Chemical Formula 3 may be one of the following compounds GEH1 to GEH30, but is not limited thereto as long as it is included in the definition of Chemical Formula 3.

[0140]

[0141]

[0142]

[0143] In addition, in the organic light emitting diode 100, the intermediate layer 130 disposed between the first electrode 110 and the second electrode 120 may have a structure including a hole injection layer (HIL) 140, a hole transport layer (HTL) 150, a light emitting layer (EML) 160, an electron transport layer (ETL) 170, and an electron injection layer (EIL) 180 in sequence from the first electrode 110. The second electrode 120 may be formed on the electron injection layer 180, and a protective film (not shown) may be formed on the second electrode 120.

[0144] In addition, although Figure 1 Although not shown in the figure, one or more of a hole transport auxiliary layer and an electron blocking layer may be added between the hole transport layer 150 and the light emitting layer 160 .

[0145] The hole transport auxiliary layer may include a compound having good hole transport properties, and the hole injection properties may be adjusted by reducing the HOMO energy level difference between the hole transport auxiliary layer 150 and the light emitting layer 160, thereby reducing the hole accumulation at the interface between the hole transport auxiliary layer and the light emitting layer 160. Therefore, the quenching phenomenon of the excitons being annihilated by polarons at the interface may be reduced. Therefore, the degradation phenomenon of the element may be reduced, thereby stabilizing the element and improving its efficiency and lifespan.

[0146] The electron blocking layer can prevent electrons from being introduced into the hole transport layer by regulating the movement of electrons and the recombination with holes, thereby improving the efficiency and life of the organic light-emitting diode. The material forming the electron blocking layer can be selected from TCTA, tris[4-(diethylamino)phenyl]amine, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, TAPC, MTDATA, mCP, mCBP, CuPC, DNTPD, TDAPB, DCDPA, 2,8-bis(9-phenyl-9H-carbazole-3-yl)dibenzo[b,d]thiophene, etc. In addition, the electron blocking layer can contain an inorganic compound. The inorganic compound can be selected from halide compounds such as LiF, NaF, KF, RbF, CsF, FrF, MgF2, CaF2, SrF2, BaF2, LiCl, NaCl, KCl, RbCl, CsCl and FrCl; and oxides such as Li2O, Li2O2, Na2O, K2O, Rb2O, Rb2O2, Cs2O, Cs2O2, LiAlO2, LiBO2, LiTaO3, LiNbO3, LiWO4, Li2CO, NaWO4, KAlO2, K2SiO3, B2O5, Al2O3 and SiO2, but is not necessarily limited thereto.

[0147] The first electrode 110 may be an anode, and may be made of ITO, IZO, tin oxide, or zinc oxide, which is a conductive material having a relatively high work function value, but is not limited thereto.

[0148] The second electrode 120 may be a cathode, and may include Al, Mg, Ca, Ag, or an alloy or combination thereof which is a conductive material having a relatively low work function value, but is not limited thereto.

[0149] The hole injection layer 140 may be positioned between the first electrode 110 and the hole transport layer 150. The hole injection layer 140 may have a function of improving the interface characteristics between the first electrode 110 and the hole transport layer 150, and may be selected as a material having appropriate conductivity. The hole injection layer 140 may include compounds such as MTDATA, CuPc, TCTA, HATCN, TDAPB, PEDOT / PSS, or N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), preferably N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1,N4,N4-triphenylbenzene-1,4-diamine), but is not limited thereto.

[0150] The hole transport layer 150 may be positioned adjacent to the light emitting layer between the first electrode 110 and the light emitting layer 160. The hole transport layer 150 may include compounds such as TPD, NPB, CBP, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, or N-(biphenyl-4-yl)-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)biphenyl-4-amine, preferably NPB, but not limited thereto.

[0151] According to one embodiment of the present disclosure, the light emitting layer 160 can be formed by doping an organic metal compound represented by Chemical Formula 1 as a dopant 160' to improve the light emitting efficiency of the main body 160" and 160'" and the element, and the dopant 160' can be used as a material emitting green light or red light, for example, as a green phosphorescent material.

[0152] According to one embodiment of the present disclosure, the doping concentration of the dopant 160' can be adjusted in the range of 1 wt% to 30 wt% based on the total weight of the two types of bodies 160" and 160'", and is not limited thereto, but for example, the doping concentration can be 2 wt% to 20 wt%, for example, 3 wt% to 15 wt%, for example, 5 wt% to 10 wt%, for example, 3 wt% to 8 wt%, for example, 2 wt% to 7 wt%, for example, 5 wt% to 7 wt%, and for example, 5 wt% to 6 wt%.

[0153] According to one embodiment of the present disclosure, the mixing ratio of the two types of hosts 160″ and 160″′ is not particularly limited, and the host 160″ of the compound represented by Chemical Formula 2 can have hole transport properties, and the host 160″′ of the compound represented by Chemical Formula 3 can have electron transport properties. Therefore, when the two types of hosts are mixed, the lifespan characteristics can be improved, and the mixing ratio of the two types of hosts can be appropriately adjusted. Therefore, the mixing ratio of the two hosts in which the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 are mixed is not particularly limited, and the ratio (based on weight) of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 can be, for example, in the range of 1:9 to 9:1, for example, 2:8, for example, 3:7, for example, 4:6, for example, 5:5, for example, 6:4, for example, 7:3, and for example 8:2.

[0154] In addition, the electron transport layer 170 and the electron injection layer 180 may be sequentially stacked between the light emitting layer 160 and the second electrode 120. The material of the electron transport layer requires high electron mobility, and electrons may be stably supplied to the light emitting layer through smooth electron transport.

[0155] For example, the material of the electron transport layer 170 is used in the art and may include, for example, compounds such as Alq3 (tris(8-hydroxyquinoline)aluminum), Liq (8-hydroxyquinoline lithium), PBD (2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4- triazole), TAZ (3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), spiro-PBD, BAlq (bis(2-methyl-8-hydroxyquinoline)-4-(phenylphenol)aluminum), SAlq, TPBi (2,2',2-(1,3,5-benzenetriyl)-tris(1-phenyl-1-H-benzimidazole), Oxadiazole, triazole, phenanthroline, benzo The invention relates to benzothiazole, benzothiazole, or 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, preferably 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, but is not limited thereto.

[0156] The electron injection layer 180 is used to smoothly inject electrons, and the material of the electron injection layer is used in the art and may include, for example, Alq3 (tris (8-hydroxyquinoline) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq, etc., but is not limited thereto. Alternatively, the electron injection layer 180 may be made of a metal compound, and the metal compound may include, for example, Liq, LiF, NaF, KF, RbF, CsF, FrF, BeF2, MgF2, CaF2, SrF2, BaF2, RaF2, etc., but is not limited thereto.

[0157] The organic light emitting diode according to the present disclosure may be a white organic light emitting diode having a series structure. In a series organic light emitting diode according to an embodiment of the present disclosure, a single light emitting stack (or light emitting portion) may be formed in a structure in which two or more light emitting stacks (or light emitting portions) are connected by a charge generation layer CGL. The organic light emitting diode may include a first electrode and a second electrode facing each other on a substrate, and two or more light emitting stacks (light emitting portions) stacked between the first electrode and the second electrode and including a light emitting layer to emit light of a specific wavelength band. A plurality of light emitting stacks (light emitting portions) may be applied to emit the same color or different colors. In addition, a light emitting stack (light emitting portion) may include one or more light emitting layers, and a plurality of light emitting layers may be light emitting layers of the same color or different colors.

[0158] In this case, one or more of the light emitting layers included in the plurality of light emitting portions may include the organic metal compound represented by Chemical Formula 1 according to the present disclosure as a dopant material. The plurality of light emitting portions in a series structure may be connected to a charge generation layer CGL formed of an N-type charge generation layer and a P-type charge generation layer.

[0159] For an exemplary embodiment of the present disclosure Figure 2 and Figure 3 2 are cross-sectional views schematically showing organic light emitting diodes having two light emitting portions and three light emitting portions in a series structure.

[0160] like Figure 2 As shown, the organic light emitting diode 100 of the present disclosure includes a first electrode 110 and a second electrode 120 facing each other, and an intermediate layer 230 positioned between the first electrode 110 and the second electrode 120. The intermediate layer 230 includes a first light emitting portion ST1 positioned between the first electrode 110 and the second electrode 120 and including a first light emitting layer 261, a second light emitting portion ST2 positioned between the first light emitting portion ST1 and the second electrode 120 and including a second light emitting layer 262, and a charge generation layer CGL positioned between the first light emitting portion ST1 and the second light emitting portion ST2. The charge generation layer CGL may include an N-type charge generation layer 291 and a P-type charge generation layer 292. One or more of the first light emitting layer 261 and the second light emitting layer 262 may include an organic metal compound represented by Chemical Formula 1 according to the present disclosure as a dopant 262'. For example, as Figure 2 As shown, the second light emitting layer 262 of the second light emitting portion ST2 may include a compound represented by Chemical Formula 1 as a dopant 262', a compound represented by Chemical Formula 2 as a hole transport type host 262", and a compound represented by Chemical Formula 3 as an electron transport type host 262''. Figure 2 Although not shown in the figure, the first light emitting portion ST1 and the second light emitting portion ST2 may each further include another light emitting layer in addition to the first light emitting layer 261 and the second light emitting layer 262. Figure 1 The contents described for the hole transport layer 150 may be applied in the same or similar manner to Figure 2 The first hole transport layer 251 and the second hole transport layer 252. Figure 1 The contents described for the electron transport layer 170 may be applied in the same or similar manner to Figure 2 The first electron transport layer 271 and the second electron transport layer 272 are formed.

[0161] like Figure 3As shown, the organic light emitting diode 100 of the present disclosure includes a first electrode 110 and a second electrode 120 facing each other, and an intermediate layer 330 positioned between the first electrode 110 and the second electrode 120. The intermediate layer 330 includes a first light emitting portion ST1 positioned between the first electrode 110 and the second electrode 120 and including a first light emitting layer 261, a second light emitting portion ST2 including a second light emitting layer 262, a third light emitting portion ST3 including a third light emitting layer 263, a first charge generation layer CGL1 positioned between the first light emitting portion ST1 and the second light emitting portion ST2, and a second charge generation layer CGL2 positioned between the second light emitting portion ST2 and the third light emitting portion ST3. The first charge generation layer CGL1 and the second charge generation layer CGL2 may include N-type charge generation layers 291 and 293 and P-type charge generation layers 292 and 294, respectively. One or more of the first light emitting layer 261, the second light emitting layer 262, and the third light emitting layer 263 may contain an organic metal compound represented by Chemical Formula 1 according to the present disclosure as a dopant. For example, as Figure 3 As shown, the second light emitting layer 262 of the second light emitting portion ST2 may include a compound represented by Chemical Formula 1 as a dopant 262', a compound represented by Chemical Formula 2 as a hole transport type host 262", and a compound represented by Chemical Formula 3 as an electron transport type host 262''. Figure 3 Although not shown, the first light emitting portion ST1, the second light emitting portion ST2 and the third light emitting portion ST3 may each be formed as a plurality of light emitting layers by including another light emitting layer in addition to the first light emitting layer 261, the second light emitting layer 262 and the third light emitting layer 263. Figure 1 The contents described for the hole transport layer 150 may be applied in the same or similar manner to Figure 3 The first hole transport layer 251, the second hole transport layer 252 and the third hole transport layer 253. Figure 1 The contents described for the electron transport layer 170 may be applied in the same or similar manner to Figure 3 The first electron transport layer 271, the second electron transport layer 272 and the third electron transport layer 273 are formed.

[0162] In addition, the organic light emitting diode according to one embodiment of the present disclosure may include a series structure in which four or more light emitting portions and three or more charge generation layers are provided between the first electrode and the second electrode.

[0163] The organic light emitting diode according to the present disclosure can be used in an organic light emitting diode display device and a lighting device using an organic light emitting diode. In one embodiment, Figure 4is a cross-sectional view schematically showing an organic light emitting diode display device to which an organic light emitting diode according to an exemplary embodiment of the present disclosure is applied.

[0164] like Figure 4 As shown, the organic light emitting diode display device 3000 may include a substrate 3010, an organic light emitting diode 4000, and a packaging film 3900 covering the organic light emitting diode 4000. On the substrate 3010, a driving thin film transistor Td as a driving element and the organic light emitting diode 4000 connected to the driving thin film transistor Td are positioned.

[0165] Although Figure 4 Although not explicitly shown, on the substrate 3010, there are also formed gate lines and data lines that cross each other to define pixel areas, power lines that are separated from and extend parallel to any one of the gate lines and the data lines, switching thin film transistors connected to the gate lines and the data lines, and a storage capacitor connected to one electrode of the switching thin film transistor and the power line.

[0166] The driving thin film transistor Td is connected to the switching thin film transistor and includes a semiconductor layer 3100 , a gate electrode 3300 , a source electrode 3520 , and a drain electrode 3540 .

[0167] The semiconductor layer 3100 may be formed on the substrate 3010 and may be made of an oxide semiconductor material or polysilicon. When the semiconductor layer 3100 is made of an oxide semiconductor material, a light blocking pattern (not shown) may be formed below the semiconductor layer 3100, and the light blocking pattern prevents light from being incident on the semiconductor layer 3100, thereby preventing degradation of the semiconductor layer 3100 caused by light. Alternatively, the semiconductor layer 3100 may be made of polysilicon, in which case both edges of the semiconductor layer 3100 may be doped with impurities.

[0168] A gate insulating film 3200 made of an insulating material is formed on the entire surface of the substrate 3010 and the semiconductor layer 3100. The gate insulating film 3200 may be made of an inorganic insulating material such as silicon oxide or silicon nitride.

[0169] A gate electrode 3300 made of a conductive material (eg, metal) is formed over the gate insulating film 3200 to correspond to the center of the semiconductor layer 3100. The gate electrode 3300 is connected to the switching thin film transistor.

[0170] An interlayer insulating film 3400 made of an insulating material is formed on the entire surface of the substrate 3010 and the gate electrode 3300. The interlayer insulating film 3400 may be made of an inorganic insulating material such as silicon oxide or silicon nitride or an organic insulating material such as benzocyclobutene or photoacryl.

[0171] The interlayer insulating film 3400 has a first semiconductor layer contact hole 3420 and a second semiconductor layer contact hole 3440 exposing both sides of the semiconductor layer 3100. The first semiconductor layer contact hole 3420 and the second semiconductor layer contact hole 3440 are positioned to be spaced apart from the gate electrode 3300 at both sides thereof.

[0172] A source electrode 3520 and a drain electrode 3540 made of a conductive material (e.g., metal) are formed on the interlayer insulating film 3400. The source electrode 3520 and the drain electrode 3540 are positioned to be spaced apart from each other relative to the gate electrode 3300, and contact both sides of the semiconductor layer 3100 through the first semiconductor layer contact hole 3420 and the second semiconductor layer contact hole 3440, respectively. The source electrode 3520 is connected to a power supply line (not shown).

[0173] The semiconductor layer 3100 , the gate electrode 3300 , the source electrode 3520 , and the drain electrode 3540 form a driving thin film transistor Td, and the driving thin film transistor Td has a coplanar structure in which the gate electrode 3300 , the source electrode 3520 , and the drain electrode 3540 are positioned above the semiconductor layer 3100 .

[0174] Alternatively, the driving thin film transistor Td may have an inverse staggered structure in which a gate electrode is positioned below a semiconductor layer and a source electrode and a drain electrode are positioned above the semiconductor layer. In this case, the semiconductor layer may be made of amorphous silicon. Meanwhile, the switching thin film transistor (not shown) may have a structure substantially the same as that of the driving thin film transistor Td.

[0175] Meanwhile, the organic light emitting diode display device 3000 may include a color filter 3600 that absorbs light generated by the organic light emitting diode 4000. For example, the color filter 3600 may absorb red (R), green (G), blue (B), and white (W) light. In this case, a red color filter pattern, a green color filter pattern, and a blue color filter pattern that absorb light may be formed separately in each pixel region, and each of the color filter patterns may be disposed to overlap with each intermediate layer 4300 of the organic light emitting diode 4000 that emits light within a wavelength band to be absorbed. By adopting the color filter 3600, the organic light emitting diode display device 3000 may realize full color.

[0176] For example, when the organic light emitting diode display device 3000 is a bottom emission type, the color filter 3600 that absorbs light may be positioned above the interlayer insulating film 3400 corresponding to the organic light emitting diode 4000. In an exemplary embodiment, when the organic light emitting diode display device 3000 is a top emission type, the color filter may be positioned above the organic light emitting diode 4000, that is, above the second electrode 4200. For example, the color filter 3600 may be formed to have a thickness of 2 μm to 5 μm.

[0177] At the same time, a planarization layer 3700 having a drain contact hole 3720 exposing the drain electrode 3540 of the driving thin film transistor Td is formed to cover the driving thin film transistor Td.

[0178] On the planarization layer 3700 , a first electrode 4100 connected to the drain electrode 3540 of the driving thin film transistor Td through the drain contact hole 3720 is separately formed in each pixel region.

[0179] The first electrode 4100 may be an anode and may be made of a conductive material having a relatively high work function value. For example, the first electrode 4100 may be made of a transparent conductive material such as ITO, IZO, or ZnO.

[0180] Meanwhile, when the organic light emitting diode display device 3000 is a top emission type, a reflective electrode or a reflective layer may be further formed under the first electrode 4100. For example, the reflective electrode or the reflective layer may be made of any one of aluminum (Al), silver (Ag), nickel (Ni), or aluminum-palladium-copper (APC) alloy.

[0181] A bank layer 3800 is formed on the planarization layer 3700 to cover the edge of the first electrode 4100. The bank layer 3800 exposes the center of the first electrode 4100 corresponding to the pixel region.

[0182] An intermediate layer 4300 is formed on the first electrode 4100. If necessary, the organic light emitting diode 4000 may have a series structure. For the series structure, reference is made to the exemplary embodiment of the present disclosure. Figures 2 to 3 and the above description.

[0183] A second electrode 4200 is formed over the substrate 3010 on which the intermediate layer 4300 is formed. The second electrode 4200 may be positioned over the entire surface of the display region and may be made of a conductive material having a relatively low work function value to serve as a cathode. For example, the second electrode 4200 may be made of any one of aluminum (Al), magnesium (Mg), and an aluminum-magnesium alloy (Al-Mg).

[0184] The first electrode 4100 , the intermediate layer 4300 , and the second electrode 4200 form an organic light emitting diode 4000 .

[0185] On the second electrode 4200, an encapsulation film 3900 is formed to prevent external moisture from penetrating into the organic light emitting diode 4000. Figure 4 Although not explicitly shown, the encapsulation film 3900 may have a three-layer structure in which a first inorganic layer, an intermediate layer, and a second inorganic layer are sequentially stacked, but is not limited thereto.

[0186] Hereinafter, embodiments of the present disclosure will be described. However, the following embodiments are merely examples of the present disclosure, and the present disclosure is not limited thereto.

[0187] Example 1

[0188] The coating will have a thickness of The glass substrate with the ITO film is washed, then ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, and dried.

[0189] After HI-1 as a hole injection material was thermally deposited in a vacuum with a thickness of 100 nm on the provided ITO transparent electrode, HT-1 as a hole transport material was thermally deposited in a vacuum with a thickness of 350 nm. Then, in the light-emitting layer, GD1 as a dopant and a mixture of GHH1 and GEH1 as a host (GHH1:GEH1=7:3, based on weight) were used, the doping concentration of the dopant was 10%, and the thickness of the light-emitting layer was 400 nm. Subsequently, after ET-1 and Liq compounds as materials for electron transport layer and electron injection layer, respectively, were thermally deposited in a vacuum, 100 nm of aluminum was deposited to form a cathode, and an organic light-emitting diode was thus manufactured.

[0190] The materials used in Example 1 are as follows.

[0191]

[0192] In the above materials, HI-1 is NPNPB, and ET-1 is ZADN.

[0193] Comparative Examples 1 to 5 and Examples 2 to 200

[0194] Organic light emitting diodes of Comparative Examples 1 to 5 and Examples 2 to 200 were manufactured in the same manner as Example 1, except that the dopant materials and host materials shown in the following Tables 1 to 15 were used in Example 1. Comparative Examples 1 to 5 each used a "CBP" type having the following structure as a host of the light emitting layer.

[0195]

[0196] Experimental example

[0197] The organic light emitting diodes manufactured in Examples 1 to 200 and Comparative Examples 1 to 5 were each connected to an external power source, and element characteristics were evaluated at room temperature using a current source and a photometer.

[0198] Specifically, with 10 mA / cm 2 The current driving voltage (V), external quantum efficiency (EQE) and lifetime (LT95) characteristics were measured, and the measured values ​​of Examples 1 to 200 were calculated as relative values ​​(percentage, %) relative to one of Comparative Examples 1 to 5, and the results are shown in Tables 1 to 15 below.

[0199] The LT95 lifetime indicates the time it takes for an organic light emitting diode to lose 5% of its initial brightness. LT95 is the most difficult device characteristic specification to meet, and is used to determine whether an image burn-in phenomenon occurs in an organic light emitting diode.

[0200] [Table 1]

[0201]

[0202]

[0203] [Table 2]

[0204]

[0205] [Table 3]

[0206]

[0207]

[0208] [Table 4]

[0209]

[0210] [Table 5]

[0211]

[0212]

[0213] [Table 6]

[0214]

[0215] [Table 7]

[0216]

[0217]

[0218] [Table 8]

[0219]

[0220] [Table 9]

[0221]

[0222] [Table 10]

[0223]

[0224] [Table 11]

[0225]

[0226] [Table 12]

[0227]

[0228]

[0229] [Table 13]

[0230]

[0231] [Table 14]

[0232]

[0233]

[0234] [Table 15]

[0235]

[0236] As can be seen from the results of Tables 1 to 15, it can be seen that the organic light-emitting diode using the organic metal compound having the structure represented by Chemical Formula 1 used in Examples 1 to 200 and satisfying the present disclosure as a dopant for the light-emitting layer and using a mixture of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 as a main body has a low driving voltage and improved external quantum efficiency (EQE) and lifetime (LT95) compared to the organic light-emitting diodes of Comparative Examples 1 to 5 using a single material as a main body.

[0237] In the organic light emitting diode according to the present disclosure, by using the organic metal compound represented by Chemical Formula 1 as a phosphorescent dopant and using a mixture of the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3 as a phosphorescent host, efficiency and lifespan characteristics can be improved and low power characteristics can be ensured by reducing driving voltage.

[0238] Effects obtainable by the present disclosure are not limited to the above-mentioned effects, and other effects that are not mentioned will be clearly understood by those skilled in the art to which the present disclosure pertains from the above description.

[0239] Although the embodiments of the present specification have been described in more detail with reference to the accompanying drawings, the present specification is not necessarily limited to these embodiments, and various modifications can be made without departing from the technical spirit of the present specification. Therefore, the embodiments disclosed in the present specification are not intended to limit the technical spirit of the present specification, but are intended to describe the present specification, and the scope of the technical spirit of the present specification is not limited by these embodiments. Therefore, it should be understood that the above-mentioned embodiments are illustrative rather than restrictive in all aspects. The scope of the present specification should be interpreted according to the attached claims, and all technical spirits within the scope of equivalents should be interpreted as included within the scope of the present specification.

[0240] Description of Reference Numerals

[0241] 100, 4000: Organic light-emitting diode

[0242] 110, 4100: First electrode

[0243] 120, 4200: Second electrode

[0244] 130, 230, 330, 4300: middle layer

[0245] 140: Hole injection layer

[0246] 150: hole transport layer, 251: first hole transport layer, 252: second hole transport layer, 253: third hole transport layer

[0247] 160: light-emitting layer, 261: first light-emitting layer, 262: second light-emitting layer, 263: third light-emitting layer 160', 262': dopant

[0248] 160”, 262”: Hole transport type body

[0249] 160”', 262”': Electron transmission type

[0250] 170: electron transport layer, 271: first electron transport layer, 272: second electron transport layer, 273: third electron transport layer

[0251] 180: Electron injection layer

[0252] 3000: Organic light-emitting diode display device

[0253] 3010: Substrate

[0254] 3100: Semiconductor layer

[0255] 3200: Gate insulation film

[0256] 3300: Gate electrode

[0257] 3400: Interlayer insulation film

[0258] 3420, 3440: first semiconductor layer contact hole and second semiconductor layer contact hole

[0259] 3520: Source electrode

[0260] 3540: Drain electrode

[0261] 3600: Color Filter

[0262] 3700: Planarization layer

[0263] 3720: Drain contact hole

[0264] 3800: Dike layer

[0265] 3900: Encapsulation film

Claims

1. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises a light-emitting layer, and the light-emitting layer comprises a dopant material and a host material, The dopant material includes an organic metal compound represented by the following Chemical Formula 1, and The host material includes a mixture of a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: [Chemical formula 1] In Chemical Formula 1, X is at least one selected from oxygen (O), sulfur (S) and selenium (Se), R1 to R6 are each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, nitrile, isonitrile, thiol, phosphine, a group formed by connecting two or more of the above groups, and combinations thereof, R7 and R8 are each independently at least one selected from the group consisting of hydrogen, deuterium, C1-C6 linear alkyl, C3-C6 branched alkyl and C3-C6 cycloalkyl, Optionally, at least one of R1 to R8 is partially or fully deuterated, a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 2 to 4, the plurality of R1s or the plurality of R2s are the same or different from each other, c and f are each independently an integer of 0 to 3, and when c and f are each independently an integer of 2 or 3, a plurality of R3 or a plurality of R6 are the same or different from each other, d is an integer from 0 to 2, and when d is an integer of 2, the plurality of R4 are the same as or different from each other, e is an integer from 0 to 5, and when e is an integer from 2 to 5, the plurality of R5 are the same as or different from each other, and m is an integer of 1 to 8, and when m is 2 or more, a plurality of R7 are the same as or different from each other, and a plurality of R8 are the same as or different from each other, and n is an integer from 0 to 2, [Chemical formula 2] In chemical formula 2, R 9a and R 9b are each independently one selected from the following: hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylamino, heteroaryl, and a group formed by connecting two or more of the above groups, or R 9a and R 9b Bonded to each other to form spirofluorene, R 10 and R 11a To R 11c are each independently one selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, amino, arylamino, aryl, heteroaryl, and a group formed by linking two or more of the above groups, L1 is one selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a divalent naphthylene group, a divalent dibenzofuranyl group, and a divalent dibenzothienyl group, Ar1 and Ar2 are each independently one selected from the group consisting of an aryl group, an arylamino group, a heteroaryl group, and a group formed by connecting two or more of the above groups, and when Ar1 and Ar2 are the group formed by connecting two or more of the above groups, two or more of the groups are connected by a single bond, an alkylene group, -O- or an alkyleneoxy group, and Optionally, Ar1 and / or Ar2 are each substituted by R a substituted, and when there is R a When R a are each independently at least one selected from the group consisting of deuterium, halogen, alkyl, alkoxy, thioalkyl, alkylsilyl, a group formed by connecting two or more of the above groups, and a combination thereof, [Chemical formula 3] In chemical formula 3, N-Het is a substituted or unsubstituted monocyclic or polycyclic heteroaryl containing one or more nitrogen, L2 is one selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C60 heteroarylene group, g is an integer from 1 to 3, and when g is 2 or more, L2 are the same as or different from each other, R 12 To R 21 each independently represents one selected from the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted phosphine oxide, and substituted or unsubstituted amine, and Optionally, R 12 To R 21 Two or more adjacent groups in the R 22 The ring structure of a substituted C6-C60 aryl group, or an unsubstituted or R 22 The ring structure of the substituted C2-C60 heteroaryl group, When there is R 22 When R 22 are each independently at least one selected from the group consisting of a C1-C20 alkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group, and h and i are each an integer from 0 to 3, and when h is 2 or greater, R 20 are the same as or different from each other, and when i is 2 or greater, R 21 The same as or different from each other. 2 . The organic light emitting diode according to claim 1 , wherein n in Chemical Formula 1 is 2. 3 . The organic light emitting diode according to claim 1 , wherein X in Chemical Formula 1 is oxygen (O). The organic light emitting diode according to claim 1 , wherein m is an integer from 1 to 3.

5. The organic light emitting diode according to claim 1, wherein the organometallic compound represented by Chemical Formula 1 is one of the following compounds GD1 to GD20: 6 . The organic light emitting diode according to claim 1 , wherein L1 in Chemical Formula 2 is one selected from a single bond and a phenylene group.

7. The organic light emitting diode according to claim 1, wherein the compound represented by Chemical Formula 2 is one of the following compounds: 8 . The organic light emitting diode according to claim 1 , wherein N—Het in Chemical Formula 3 is a substituted or unsubstituted triazine group. 9 . The organic light emitting diode according to claim 8 , wherein N—Het in Chemical Formula 3 represents a triazine group mono- or di-substituted with a substituent selected from a phenyl group, a biphenyl group, and a naphthyl group. 10 . The organic light emitting diode according to claim 1 , wherein L2 in Chemical Formula 3 is a single bond.

11. The organic light emitting diode according to claim 1, wherein the compound represented by Chemical Formula 3 is one of the following compounds GEH1 to GEH30: 12 . The organic light emitting diode according to claim 1 , wherein the intermediate layer further comprises any one or more of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, an electron transport layer and an electron injection layer.

13. An organic light emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and one or more light emitting portions positioned between the first electrode and the second electrode, wherein at least one of the light-emitting portions comprises a green phosphorescent light-emitting layer, The green phosphorescent light-emitting layer comprises a dopant material and a host material, The dopant material includes an organic metal compound represented by the following Chemical Formula 1, and The host material includes a compound represented by the following Chemical Formula 2 and a compound represented by the following Chemical Formula 3: [Chemical formula 1] In Chemical Formula 1, X is at least one selected from oxygen (O), sulfur (S) and selenium (Se), R1 to R6 are each independently at least one selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, nitrile, isonitrile, thiol, phosphine, a group formed by connecting two or more of the above groups, and combinations thereof, R7 and R8 are each independently at least one selected from the group consisting of hydrogen, deuterium, C1-C6 linear alkyl, C3-C6 branched alkyl and C3-C6 cycloalkyl, Optionally, at least one of R1 to R8 is partially or fully deuterated, a and b are each independently an integer of 0 to 4, and when a and b are each independently an integer of 2 to 4, the plurality of R1s or the plurality of R2s are the same or different from each other, c and f are each independently an integer of 0 to 3, and when c and f are each independently an integer of 2 or 3, a plurality of R3 or a plurality of R6 are the same or different from each other, d is an integer from 0 to 2, and when d is an integer of 2, the plurality of R4 are the same as or different from each other, e is an integer from 0 to 5, and when e is an integer from 2 to 5, the plurality of R5 are the same as or different from each other, and m is an integer of 1 to 8, and when m is 2 or more, a plurality of R7 are the same as or different from each other, and a plurality of R8 are the same as or different from each other, and n is an integer from 0 to 2, [Chemical formula 2] In chemical formula 2, R 9a and R 9b are each independently one selected from the following: hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylamino, heteroaryl, and a group formed by connecting two or more of the above groups, or R 9a and R 9b Bonded to each other to form spirofluorene, R 10 and R 11a To R 11c are each independently one selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, thioalkyl, cycloalkyl, alkenyl, alkynyl, amino, arylamino, aryl, heteroaryl, and a group formed by linking two or more of the above groups, L1 is one selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a divalent naphthylene group, a divalent dibenzofuranyl group, and a divalent dibenzothienyl group, Ar1 and Ar2 are each independently one selected from the group consisting of an aryl group, an arylamino group, a heteroaryl group, and a group formed by connecting two or more of the above groups, and when Ar1 and Ar2 are the group formed by connecting two or more of the above groups, two or more of the groups are connected by a single bond, an alkylene group, -O- or an alkyleneoxy group, and Optionally, Ar1 and / or Ar2 are each substituted by R a substituted, and when there is R a When R a are each independently at least one selected from the group consisting of deuterium, halogen, alkyl, alkoxy, thioalkyl, alkylsilyl, a group formed by connecting two or more of the above groups, and a combination thereof, [Chemical formula 3] In chemical formula 3, N-Het is a substituted or unsubstituted monocyclic or polycyclic heteroaryl containing one or more nitrogen, L2 is one selected from the group consisting of a single bond, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C2-C60 heteroarylene group, g is an integer from 1 to 3, and when g is 2 or more, L2 are the same as or different from each other, R 12 To R 21 each independently represents one selected from the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted phosphine oxide, and substituted or unsubstituted amine, and Optionally, R 12 To R 21 Two or more adjacent groups in the R 22 The ring structure of a substituted C6-C60 aryl group, or an unsubstituted or R 22 The ring structure of the substituted C2-C60 heteroaryl group, When there is R 22 When R 22 are each independently at least one selected from the group consisting of a C1-C20 alkyl group, a C6-C30 aryl group, and a C3-C30 heteroaryl group, and h and i are each an integer from 0 to 3, and when h is 2 or greater, R 20 are the same as or different from each other, and when i is 2 or greater, R 21 The same as or different from each other.

14. The organic light emitting diode according to claim 13, wherein the organometallic compound represented by Chemical Formula 1 is one of the following compounds GD1 to GD20:

15. The organic light emitting diode according to claim 13, wherein the compound represented by Chemical Formula 2 is one of the following compounds:

16. The organic light emitting diode according to claim 13, wherein the compound represented by Chemical Formula 3 is one of the following compounds GEH1 to GEH30:

17. The organic light emitting diode according to claim 13, wherein a plurality of light emitting portions are present between the first electrode and the second electrode, and The plurality of light-emitting sections form a structure connected by a charge generation layer provided between the plurality of light-emitting sections.

18. An organic light emitting diode display device, comprising: substrate; a drive element positioned on the substrate; as well as An organic light emitting diode according to any one of claims 1 to 17 positioned on the substrate and connected to the driving element.

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