IP Library Patent Application 15545577
Patent Application
App. No. 15/545,577

DOUBLE-SPIRO TYPE COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE CONTAINING SAME

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Quick Facts
Patent No.
US None
App. No.
15/545,577
Abstract

The present specification relates to a double spiro structure compound, and an organic light emitting device comprising the same.

Claims (974)

1 . A double spiro structure compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 is represented by any one of the following Chemical Formula A to Chemical Formula C,

wherein, in Chemical Formula A to Chemical Formula C,

X 1 to X 3 are the same as or different from each other, and each independently CH or N;

at least one of X 1 to X 3 is N;

X 4 is O, S or NAr 5 ;

L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;

Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and

Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.

2 . The double spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-3:

wherein, in Chemical Formula 1-1 to Chemical Formula 1-3,

a definition of R 1 is the same as in Chemical Formula 1.

3 . The double spiro structure compound of claim 1 , wherein Cy1 is a substituted or unsubstituted benzene ring.

4 . The double spiro structure compound of claim 1 , wherein L 1 to L 3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.

5 . The double spiro structure compound of claim 1 , wherein Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.

6 . The double spiro structure compound of claim 1 , wherein Ar 1 to Ar 5 are the same as or different from each other, and each independently selected as any one among the following structural formulae:

wherein, in the structural formulae, means a site linking to other substituents.

7 . The double spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L 1 , Ar 1 and Ar 2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1:

TABLE 1

− − −L 1 − − −

− − −Ar 1

− − −Ar 2

2-1- 1

Direct bond

2-1- 2

Direct bond

2-1- 3

Direct bond

2-1- 4

Direct bond

2-1- 5

Direct bond

2-1- 6

Direct bond

2-1- 7

Direct bond

2-1- 8

Direct bond

2-1- 9

Direct bond

2-1- 10

Direct bond

2-1- 11

Direct bond

2-1- 12

Direct bond

2-1- 13

Direct bond

2-1- 14

Direct bond

2-1- 15

Direct bond

2-1- 16

Direct bond

2-1- 17

Direct bond

2-1- 18

Direct bond

2-1- 19

Direct bond

2-1- 20

Direct bond

2-1- 21

Direct bond

2-1- 22

Direct bond

2-1- 23

Direct bond

2-1- 24

Direct bond

2-1- 25

Direct bond

2-1- 26

Direct bond

2-1- 27

Direct bond

2-1- 28

Direct bond

2-1- 29

Direct bond

2-1- 30

Direct bond

2-1- 31

Direct bond

2-1- 32

Direct bond

2-1- 33

Direct bond

2-1- 34

Direct bond

2-1- 35

Direct bond

2-1- 36

Direct bond

2-1- 37

Direct bond

2-1- 38

Direct bond

2-1- 39

Direct bond

2-1- 40

Direct bond

2-1- 41

Direct bond

2-1- 42

Direct bond

2-1- 43

Direct bond

2-1- 44

Direct bond

2-1- 45

Direct bond

2-1- 46

Direct bond

2-1- 47

Direct bond

2-1- 48

Direct bond

2-1- 49

Direct bond

2-1- 50

Direct bond

2-1- 51

Direct bond

2-1- 52

Direct bond

2-1- 53

Direct bond

2-1- 54

Direct bond

2-1- 55

Direct bond

2-1- 56

Direct bond

2-1- 57

Direct bond

2-1- 58

Direct bond

2-1- 59

Direct bond

2-1- 60

Direct bond

2-1- 61

Direct bond

2-1- 62

Direct bond

2-1- 63

Direct bond

2-1- 64

2-1- 65

2-1- 66

2-1- 67

2-1- 68

2-1- 69

2-1- 70

2-1- 71

2-1- 72

2-1- 73

2-1- 74

2-1- 75

2-1- 76

2-1- 77

2-1- 78

2-1- 79

2-1- 80

2-1- 81

2-1- 82

2-1- 83

2-1- 84

2-1- 85

2-1- 86

2-1- 87

2-1- 88

2-1- 89

2-1- 90

2-1- 91

2-1- 92

2-1- 93

2-1- 94

2-1- 95

2-1- 96

2-1- 97

2-1- 98

2-1- 99

2-1- 100

2-1- 101

2-1- 102

2-1- 103

2-1- 104

2-1- 105

2-1- 106

2-1- 107

2-1- 108

2-1- 109

2-1- 110

2-1- 111

2-1- 112

2-1- 113

2-1- 114

2-1- 115

2-1- 116

2-1- 117

2-1- 118

2-1- 119

2-1- 120

2-1- 121

2-1- 122

2-1- 123

2-1- 124

2-1- 125

2-1- 126

2-1- 127

2-1- 128

2-1- 129

2-1- 130

2-1- 131

2-1- 132

2-1- 133

2-1- 134

2-1- 135

2-1- 136

2-1- 137

2-1- 138

2-1- 139

2-1- 140

2-1- 141

2-1- 142

2-1- 143

2-1- 144

2-1- 145

2-1- 146

2-1- 147

2-1- 148

2-1- 149

2-1- 150

2-1- 151

2-1- 152

2-1- 153

2-1- 154

2-1- 155

2-1- 156

2-1- 157

2-1- 158

2-1- 159

2-1- 160

2-1- 161

2-1- 162

2-1- 163

2-1- 164

2-1- 165

2-1- 166

2-1- 167

2-1- 168

2-1- 169

2-1- 170

2-1- 171

2-1- 172

2-1- 173

2-1- 174

2-1- 175

2-1- 176

2-1- 177

2-1- 178

2-1- 179

2-1- 180

2-1- 181

2-1- 182

2-1- 183

2-1- 184

2-1- 185

2-1- 186

2-1- 187

2-1- 188

2-1- 189

2-1- 190

2-1- 191

2-1- 192

2-1- 193

2-1- 194

2-1- 195

2-1- 196

2-1- 197

2-1- 198

2-1- 199

2-1- 200

2-1- 201

2-1- 202

2-1- 203

2-1- 204

2-1- 205

2-1- 206

2-1- 207

2-1- 208

2-1- 209

2-1- 210

2-1- 211

2-1- 212

2-1- 213

2-1- 214

2-1- 215

2-1- 216

2-1- 217

2-1- 218

2-1- 219

2-1- 220

2-1- 221

2-1- 222

2-1- 223

2-1- 224

2-1- 225

2-1- 226

2-1- 227

2-1- 228

2-1- 229

2-1- 230

2-1- 231

2-1- 232

2-1- 233

2-1- 234

2-1- 235

2-1- 236

2-1- 237

2-1- 238

2-1- 239

2-1- 240

2-1- 241

2-1- 242

2-1- 243

2-1- 244

2-1- 245

2-1- 246

2-1- 247

2-1- 248

2-1- 249

2-1- 250

2-1- 251

2-1- 252

2-1- 253

2-1- 254

2-1- 255

2-1- 256

2-1- 257

2-1- 258

2-1- 259

2-1- 260

2-1- 261

2-1- 262

2-1- 263

2-1- 264

2-1- 265

2-1- 266

2-1- 267

2-1- 268

2-1- 269

2-1- 270

2-1- 271

2-1- 272

2-1- 273

+-

2-1- 274

2-1- 275

2-1- 276

2-1- 277

2-1- 278

2-1- 279

2-1- 280

2-1- 281

2-1- 282

2-1- 283

2-1- 284

2-1- 285

2-1- 286

2-1- 287

2-1- 288

2-1- 289

2-1- 290

2-1- 291

2-1- 292

2-1- 293

2-1- 294

2-1- 295

2-1- 296

2-1- 297

2-1- 298

2-1- 299

2-1- 300

2-1- 301

2-1- 302

2-1- 303

2-1- 304

2-1- 305

2-1- 306

2-1- 307

2-1- 308

2-1- 309

2-1- 310

2-1- 311

2-1- 312

2-1- 313

2-1- 314

2-1- 315

2-1- 316

2-1- 317

2-1- 318

2-1- 319

2-1- 320

2-1- 321

2-1- 322

2-1- 323

2-1- 324

2-1- 325

2-1- 326

2-1- 327

2-1- 328

2-1- 329

2-1- 330

2-1- 331

2-1- 332

2-1- 333

2-1- 334

8 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L 2 , Ar 3 and Ar 4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2:

TABLE 2

3-1-1

Direct bond

3-1-2

Direct bond

3-1-3

Direct bond

3-1-4

Direct bond

3-1-5

Direct bond

3-1-6

Direct bond

3-1-7

Direct bond

3-1-8

Direct bond

3-1-9

Direct bond

3-1-10

Direct bond

3-1-11

Direct bond

3-1-12

3-1-13

3-1-14

3-1-15

3-1-16

3-1-17

3-1-18

3-1-19

3-1-20

3-1-21

3-1-22

3-1-23

3-1-24

3-1-25

3-1-26

3-1-27

3-1-28

3-1-29

3-1-30

3-1-31

3-1-32

3-1-33

3-1-34

3-1-35

3-1-36

3-1-37

3-1-38

3-1-39

3-1-40

3-1-41

3-1-42

3-1-43

3-1-44

3-1-45

3-1-46

3-1-47

3-1-48

3-1-49

3-1-50

3-1-51

3-1-52

3-1-53

3-1-54

3-1-55

3-1-56

3-1-57

3-1-58

3-1-59

3-1-60

3-1-61

3-1-62

3-1-63

3-1-64

3-1-65

3-1-66

3-1-67

3-1-68

3-1-69

3-1-70

3-1-71

3-1-72

3-1-73

3-1-74

3-1-75

3-1-76

3-1-77

3-1-78

3-1-79

3-1-80

3-1-81

3-1-82

3-1-83

3-1-84

3-1-85

3-1-86

3-1-87

3-1-88

3-1-89

3-1-90

3-1-91

3-1-92

3-1-93

3-1-94

3-1-95

3-1-96

3-1-97

3-1-98

3-1-99

3-1-100

3-1-101

3-1-102

3-1-103

3-1-104

9 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L 2 , Ar 3 and Ar 4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3:

TABLE 3

− − −L 2 − − −

− − −Ar 3

− − −Ar 4 − − −

3-2-1

Direct bond

3-2-2

Direct bond

3-2-3

Direct bond

3-2-4

Direct bond

3-2-5

Direct bond

3-2-6

Direct bond

3-2-7

Direct bond

3-2-8

Direct bond

3-2-9

Direct bond

3-2-10

Direct bond

3-2-11

Direct bond

3-2-12

3-2-13

3-2-14

3-2-15

3-2-16

3-2-17

3-2-18

3-2-19

3-2-20

3-2-21

3-2-22

3-2-23

3-2-24

3-2-25

3-2-26

3-2-27

3-2-28

3-2-29

3-2-30

3-2-31

3-2-32

3-2-33

3-2-34

3-2-35

3-2-36

3-2-37

3-2-38

3-2-39

3-2-40

3-2-41

3-2-42

3-2-43

3-2-44

3-2-45

3-2-46

3-2-47

3-2-48

3-2-49

3-2-50

3-2-51

3-2-52

3-2-53

3-2-54

3-2-55

3-2-56

3-2-57

3-2-58

3-2-59

3-2-60

3-2-61

3-2-62

3-2-63

3-2-64

3-2-65

3-2-66

3-2-67

3-2-68

3-2-69

3-2-70

3-2-71

3-2-72

3-2-73

3-2-74

3-2-75

3-2-76

3-2-77

3-2-78

3-2-79

3-2-80

3-2-81

3-2-82

3-2-83

3-2-84

3-2-85

3-2-86

3-2-87

3-2-88

3-2-89

3-2-90

3-2-91

3-2-92

3-2-93

3-2-94

3-2-95

3-2-96

3-2-97

3-2-98

3-2-99

3-2-100

3-2-101

3-2-102

3-2-103

3-2-104

10 . The double Spiro structure compound of claim 1 , wherein in the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L 2 , Ar 3 and Ar 4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4:

TABLE 4

− − −L 4 − − −

− − −Ar 3

− − −Ar 4

3-3-1

Direct bond

3-3-2

Direct bond

3-3-3

Direct bond

3-3-4

Direct bond

3-3-5

Direct bond

3-3-6

Direct bond

3-3-7

Direct bond

3-3-8

Direct bond

3-3-9

Direct bond

3-3-10

Direct bond

3-3-11

Direct bond

3-3-12

3-3-13

3-3-14

3-3-15

3-3-16

3-3-17

3-3-18

3-3-19

3-3-20

3-3-21

3-3-22

3-3-23

3-3-24

3-3-25

3-3-26

3-3-27

3-3-28

3-3-29

3-3-30

3-3-31

3-3-32

3-3-33

3-3-34

3-3-35

3-3-36

3-3-37

3-3-38

3-3-39

3-3-40

3-3-41

3-3-42

3-3-43

3-3-44

3-3-45

3-3-46

3-3-47

3-3-48

3-3-49

3-3-50

3-3-51

3-3-52

3-3-53

3-3-54

3-3-55

3-3-56

3-3-57

3-3-58

3-3-59

3-3-60

3-3-61

3-3-62

3-3-63

3-3-64

3-3-65

3-3-66

3-3-67

3-3-68

3-3-69

3-3-70

3-3-71

3-3-72

3-3-73

3-3-74

3-3-75

3-3-76

3-3-77

3-3-78

3-3-79

3-3-80

3-3-81

3-3-82

3-3-83

3-3-84

3-3-85

3-3-86

3-3-87

3-3-88

3-3-89

3-3-90

3-3-91

3-3-92

3-3-93

3-3-94

3-3-95

3-3-96

3-3-97

3-3-98

3-3-99

3-3-100

3-3-101

3-3-102

3-3-103

3-3-104

11 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L 2 , Ar 3 and Ar 4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5:

TABLE 5

—L 2—

—Ar 3

—Ar 4

3-4-1 

Direct bond

3-4-2 

Direct bond

3-4-3 

Direct bond

3-4-4 

Direct bond

3-4-5 

Direct bond

3-4-6 

Direct bond

3-4-7 

Direct bond

3-4-8 

Direct bond

3-4-9 

Direct bond

3-4-10 

Direct bond

3-4-11 

Direct bond

3-4-12 

3-4-13 

3-4-14 

3-4-15 

3-4-16 

3-4-17 

3-4-18 

3-4-19 

3-4-20 

3-4-21 

3-4-22 

3-4-23 

3-4-24 

3-4-25 

3-4-26 

3-4-27 

3-4-28 

3-4-29 

3-4-30 

3-4-31 

3-4-32 

3-4-33 

3-4-34 

3-4-35 

3-4-36 

3-4-37 

3-4-38 

3-4-39 

3-4-40 

3-4-41 

3-4-42 

3-4-43 

3-4-44 

3-4-45 

3-4-46 

3-4-47 

3-4-48 

3-4-49 

3-4-50 

3-4-51 

3-4-52 

3-4-53 

3-4-54 

3-4-55 

3-4-56 

3-4-57 

3-4-58 

3-4-59 

3-4-60 

3-4-61 

3-4-62 

3-4-63 

3-4-64 

3-4-65 

3-4-66 

3-4-67 

3-4-68 

3-4-69 

3-4-70 

3-4-71 

3-4-72 

3-4-73 

3-4-74 

3-4-75 

3-4-76 

3-4-77 

3-4-78 

3-4-79 

3-4-80 

3-4-81 

3-4-82 

3-4-83 

3-4-84 

3-4-85 

3-4-86 

3-4-87 

3-4-88 

3-4-89 

3-4-90 

3-4-91 

3-4-92 

3-4-93 

3-4-94 

3-4-95 

3-4-96 

3-4-97 

3-4-98 

3-4-99 

3-4-100

3-4-101

3-4-102

3-4-103

3-4-104

12 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L 3 and X 4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6:

TABLE 6

X 4

—L 3 —

4-4-1

O

4-4-2

S

X 4

—L 3 —

—Ar 5

4-4-3 

NAr 5

4-4-4 

NAr 5

4-4-5 

NAr 5

4-4-6 

NAr 5

4-4-7 

NAr 5

4-4-8 

NAr 5

4-4-9 

NAr 5

4-4-10

NAr 5

4-4-11

NAr 5

4-4-12

NAr 5

4-4-13

NAr 5

4-4-14

NAr 5

4-4-15

NAr 5

4-4-16

NAr 5

4-4-17

NAr 5

4-4-18

NAr 5

4-4-19

NAr 5

4-4-20

NAr 5

4-4-21

NAr 5

4-4-22

NAr 5

13 . An organic light emitting device comprising:

an anode;

a cathode provided opposite to the anode; and

a light emitting layer and one or more organic material layers provided between the anode and the cathode,

wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound of claim 1 .

14 . The organic light emitting device of claim 13 , wherein the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the double spiro structure compound.

15 . The organic light emitting device of claim 13 , wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the double spiro structure compound.

16 . The organic light emitting device of claim 13 , wherein the light emitting layer comprises the double spiro structure compound.

17 . The organic light emitting device of claim 13 , wherein the organic material layer comprises an electron transfer layer, an electron injection layer or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound.

18 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2:

wherein, in Chemical Formula 2,

L 1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and

Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

19 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the light emitting layer or the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 3:

wherein, in Chemical Formula 3,

X 1 to X 3 are the same as or different from each other, and each independently CH or N;

at least one of X 1 to X 3 is N;

L 2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and

Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

20 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4:

wherein, in Chemical Formula 4,

X 4 is O, S or NAr 5 ;

L 3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;

Ar 5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and

Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 21, 2017
From: CHA, YONGBUM; KIM, JIN JOO
To: LG CHEM, LTD.
Reel/Frame 043302/0020 →